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A Novel Process For The Preparation Of N Chloro Bis Benzene Sulfonimide

Abstract: The present invention relates to a novel process for the preparation of N-Chloro bis benzene sulfonamide/N-Chloro substituted bis benzene sulfonamide of formula I or intermediates or polymorphs or salts thereof, Wherein, R1and R2 represents H, alkyl, alkenyl, alkynyl, cyclic alkyl haloalkyl, halogen, nitro, hydroxy, alkoxy, alkylthio, sulfur, sulfoxy, carboxy, cyano, amide, aryl, aralkyl, aralkenyl, alkaryl. m and n represent an integer from 0-5.

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Patent Information

Application #
Filing Date
17 July 2018
Publication Number
32/2021
Publication Type
INA
Invention Field
ELECTRICAL
Status
Email
intellexempire@gmail.com
Parent Application

Applicants

LOBA CHEMIE PRIVATE LIMITED
107, Woodhouse Road, Meherjit Co- Soc. Ltd, Colaba, Mumbai City, Mumbai-400005, Maharashtra, India.

Inventors

1. Palav Amey V.
G/202, Gokul Horizon Thakur Village, Kandivali (E), Mumbai-400101, Maharashtra, India.
2. Dr. Parab Vinod L.
B-1508, Lords, Bhandup (W), Mumbai-400078, Maharashtra, India.
3. Dr. Chturbhuj Ganesh U
Nathalal Parekh Marg, Near Khalsa College, Matunga, Mumbai-400019, Maharashtra, India.

Specification

FORM 2 THE PATENTS ACT, 1970
(39 of 1970)
& THE PATENTS RULES, 2003 COMPLETE SPECIFICATION
[See section 10 and rule 13]
1. TITLE OF THE INVENTION:
A NOVEL PROCESS FOR THE PREPARATION OF N-CHLORO BIS BENZENE SULFONIMIDE
2. APPLICANT:
(a) Name : LOBA CHEMIE PRIVATE LIMITED
(b) Nationality: An Indian Registered Company
(c) Address : 107, Woodhouse Road, Meherjit Co- Soc. Ltd, Colaba, Mumbai City, Mumbai-400005, Maharashtra, India.
THE FOLLOWING SPECIFICATION DESCRIBES THE INVENTION AND THE MANNER IN WHICH IT IS TO BE PERFORMED.

FIELD OF THE INVENTION
The present invention relates to a novel process for the preparation of N-Chloro bis benzene sulfonamide/N-Chloro substituted bis benzene sulfonamide of formula I or intermediates or polymorphs or salts thereof,

Wherein,
R1and R2 represents H, alkyl, alkenyl, alkynyl, cyclic alkyl haloalkyl, halogen, nitro,
hydroxy, alkoxy, alkylthio, sulfur, sulfoxy, carboxy, cyano, amide, aryl, aralkyl,
aralkenyl, alkaryl;
m and n represent an integer from 0-5.
BACKGROUND OF THE INVENTION
N-Chloro bis benzene sulfonimide also known as by names Dibenzenesulfonamide,
N-chloro- (7CI,8CI); N-Chloro-N-(phenylsulfonyl)benzenesulfonamide; N-
Chlorodibenzenesulfonimide, is a operationally convenient, bench stable,
regioselective chlorinating reagent with optimum BDE (bond dissociation energy) which would generate electrophile (Cl+) without any protonation, additive, or Lewis acid. The calculated BDE for N-Chloro bis benzene sulfonimide is 39.8Kcal mol-1, which is drastically less than commercially available N-Chloro Succinimide 58Kcal mol-1 having a great difference of 18.2Kcal mol-1. Also, Bis benzene sulfonamide has lower pKa value of 1.45 and higher N-Cl bond length of 1.8A compared to N-Chloro Succinimide (pKa 10.52) and N-Cl Bond length (1.62A). This theoretical study reveals that N-Chloro bis benzene sulfonimide is a more electrophilic than N-Chloro

Succinimide. Because of these superiority of N-Chloro bis benzene sulfonimide over to other available chlorinating reagents such as molecular Cl2 or SOCl2, Cl2/1°, 2°, 3° amines, H2O2/HCl, SnCl4/Pb(OAc)4, InCl3/NaClO, (Alkyl)4PPh3+Cl-, KCl/Oxone, Sulfuryl Chloride, metal chloride/H2O2, N-Chloro Succinimide, N-Chloro Saccharin, Chloramine T, N-Chloropthalamide, 1,3 Dichloro-5,5-dimethyl hydantoin(DCDMH), Trichloroisocyanuric acid(TCIAA), it is gaining attraction of scientific community recently. It can serve as an excellent chlorinating reagent for aromatic as well as heterocyclic molecules without activating it, i.e., it doesn’t require any Lewis acid or Bronsted acid, or any inorganic acid for protonation. It itself in the selected solvent serves as chlorine donor. The introduction of chlorine onto aromatic ring is a significant synthetic transformation because chlorinated compounds are acknowledged as versatile initial materials and added ingredient in the manufacture of high eminence insecticides, fungicides, selective weedicides, bulk drugs, industrial chemicals, pharmaceutical etc. Further structure modification of N-Chloro bis benzene sulfonimide by changing the substituent in the benzene ring supplies one possible approach to improve its chlorinating reactivity and selectivity.
Although in literature a very few methods to prepare this important chlorinating reagents is known but there was no promising and effective approach for synthesizing N-Chloro bis benzene sulfonimide and its analogues is described. Japanese patent application JP 2016204367A assigned to Nippon Soda Co., Ltd., Japan, discloses the preparation of N-Chloro bis benzene sulfonimide from bis benzene sulfonamide using chlorinating agent sodium hypochlorite and potassium hypochlorite.
In Chinese patent CN 105669503B assigned to Sun Yat-Sen University, Peop. Rep. China, Chloro bis benzene sulfonimide is prepared using the reagent t-butyl hypochlorite although t-butyl hypochlorite being an organic hypochlorites are not stable even at room temperature, they start decomposition with hazardous gases like methyl chloride and poses a storage problem.

In research Journal’s article Khimiko-FarmatsevticheskiiZhurnal, Volume: 10, Issue: 6, Pages: 60-1, year: 1976, (P-RC6H4SO2)2NCl (I; R = H, Me, NO2, F, Cl, Br, S) were prepared in 88-95% yield by treatment of (p-RC6H4SO2)2NNa with Cl. In this process use of molecular chlorine (Cl2 gas) is disclosed which is hazardous because excess of chlorine is difficult to quench.
Keeping in view of available literature procedures to prepare N-Chloro bis benzene sulfonimide and analogues, inventors of the present invention has developed a promising and effective approach for synthesizing N-Chloro bis benzene sulfonimide and analogues using chlorination of bis benzene sulfonamide/substituted bis benzene sulfonamide with inorganic hypochlorites along with oxidant oxone. The invented process presents a various advantage over prior art processes and gives the highly pure product in higher yield.
OBJECTIVE OF THE INVENTION
The objective of present invention is to provide a novel process for the preparation of N-Chloro bis benzene sulfonimide/N-Chloro substituted bis benzene sulfonimide of formula I or intermediates or polymorphs or salts thereof.
Another objective of present invention is to provide a novel process for the preparation of N-Chloro bis benzene sulfonimide of formula I.
Yet another objective of present invention is to provide a novel process for the preparation of N-Chloro substituted bis benzene sulfonimide of formula I.
Further objective of the present invention is to provide a novel process for the preparation of N-Chloro bis benzene sulfonimide/N-Chloro substituted bis benzene sulfonimide of formula I in quantitative yield and high purity.

Further objective of present invention is to provide a novel process for the preparation of N-Chloro bis benzene sulfonimide/N-Chloro substituted bis benzene sulfonimide of formula I using commercially available raw materials and using industrial viable process.
BRIEF DESCRIPTION OF THE DRAWINGS
Figure 1: HPLC graph of N-Chloro bis benzene sulfonimide Figure 2: HRMS Graph of N-Chloro bis benzene sulfonimide Figure 3: IR Spectra of N-Chloro bis benzene sulfonimide

DETAILED DESCRIPTION OF THE INVENTION
Accordingly, the present invention provides a novel process for the preparation of N-Chloro bis benzene sulfonimide/N-Chloro substituted bis benzene sulfonimide of formula I or intermediates or polymorphs or salts thereof.
Accordingly, the present invention relates to the process of the preparation of compounds of general formula (I),

Wherein,
R1and R2 represents H, alkyl, alkenyl, alkynyl, cyclic alkyl haloalkyl, halogen, nitro,
hydroxy, alkoxy, alkylthio, sulfur, sulfoxy, carboxy, cyano, amide, aryl, aralkyl,
aralkenyl, alkaryl.
m and n represent an integer from 0-5.
According to one other embodiment, compounds of general formula (I) is prepared by the process described in below scheme 1:

Scheme 1: Process for the preparation of N-Chloro bis benzene sulfonimide/N-Chloro substituted bis benzene sulfonimide

Wherein,
R1and R2 represents H, alkyl, alkenyl, alkynyl, cyclic alkyl haloalkyl, halogen, nitro,
hydroxy, alkoxy, alkylthio, sulfur, sulfoxy, carboxy, cyano, amide, aryl, aralkyl,
aralkenyl, alkaryl.
m and n represent an integer from 0-5.
A=Sodium hypochlorite/Potassium hypochlorite/Ammonium chloride/Lithium
chloride
B=Sodium bicarbonate/Sodium carbonate/Ammonium carbonate
According to another embodiment, the present invention provides a novel process for the preparation of N-Chloro bis benzene sulfonimide/N-Chloro substituted bis benzene sulfonimide of formula I or intermediates or polymorphs or salts thereof which comprises steps of:
a) charging the reagent, A in reaction vessel;
b) charging the bis benzene sulfonimide or substituted bis benzene sulfonimide in a reaction vessel of step a);
c) stirring the solution of step b) for a suitable time at suitable temperature;
d) adding slowly reagent, B to the reaction mixture of step c);
e) maintaining the suitable reaction temperature of step d);
f) adding slowly the aqueous oxone solution in a reaction mass of step e);
g) maintaining the suitable reaction temperature of step f);
h) stirring the solution of step g) for a suitable time at suitable temperature; i) filtering the resultant mass of step h); and j) drying the resultant mass of step i)
According to one another embodiment, the present invention provides a novel process for the preparation of N-Chlorobis benzene sulfonimide/N-Chloro substituted bis benzene sulfonimide of formula I in quantitative yield and high purity.

According to one another embodiment, the present invention provides a novel process for the preparation of N-Chloro bis benzene sulfonimide/N-Chloro substituted bis benzene sulfonimide of formula I using commercially available raw materials and using industrial viable process.
As used herein, N-Chloro substituted bis benzene sulfonimide refers to N-Chloro bis benzene sulfonimide wherein one or both benzene ring may be substituted at any carbon position by groups selected from alkyl, alkenyl, alkynyl, cyclic alkyl haloalkyl, halogen, nitro, hydroxy, alkoxy, alkylthio, sulfur, sulfoxy, carboxy, cyano, amide, aryl, aralkyl, aralkenyl, alkaryl and the like.
As used herein, N-Chloro substituted bis benzene sulfonimide refers to N-Chloro bis benzene sulfonimide wherein one or both benzene ring may be substituted at any carbon position by groups selected from alkyl, alkenyl, alkynyl, cyclic alkyl haloalkyl, halogen, nitro, hydroxy, alkoxy, alkylthio, sulfur, sulfoxy, carboxy, cyano, amide, aryl, aralkyl, aralkenyl, alkaryl and the like having identical or unidentical group in benzene rings.
In the above description, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl" includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers.
"Alkenyl" includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl" also includes polyenes such as 1, 2-propadienyl and 2, 4-hexadienyl.
"Alkynyl" includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. "Alkynyl" can also

include moieties comprised of multiple triple bonds such as 2, 5-hexadiynyl.
"Cyclic alkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Cyclic alkenyl includes, for example, cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl. Cyclic alkynyl, similarly refers to cyclic pentynyl, hexynyl, heptynyl and octynyl.
The term “aryl” as used herein is a group that contains any carbon-based aromatic group including, but not limited to, benzene, naphthalene, phenyl, biphenyl, anthracene, and the like. The aryl group can be substituted or unsubstituted. In addition, the aryl group can be a single ring structure or comprise multiple ring structures that are either fused ring structures or attached via one or more bridging groups such as a carbon-carbon bond.
The term "aralkyl" refers to aryl hydrocarbon radicals including an alkyl portion as defined above. Examples include benzyl, phenylethyl, and 6-napthylhexyl. As used herein, the term "aralkenyl" refers to aryl hydrocarbon radicals including an alkenyl portion, as defined above, and an aryl portion, as defined above. Examples include styryl, 3-(benzyl) prop-2-enyl, and 6-napthylhex-2-enyl.
The term "alkaryl" refers to an aryl group which bears an alkyl group; as used herein, the term "alkaryl" includes both substituted and unsubstituted groups. One example of an alkaryl group is the 4-methylphenyl radical.
"Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
"Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
"Sulfoxy" refers tosulfoxy containing compounds including sulfate,

sulfonate, and sulfone compounds.
"Carboxy" refers to –COOH containing groups.
"Amide" refers to -C and –N amide groups such as carbamoyl and formamide groups.
The term "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine.
As described herein the present invention relates to a novel process for the preparation of N-Chloro bis benzene sulfonimide/N-Chloro substituted bis benzene sulfonimide or intermediates or polymorphs or salts thereof of general formula (I) using chlorinating agent and oxone system. Particularly the present invention provides an industrial viable process for preparation of N-Chloro bis benzene sulfonimide in quantitative yield and high purity. Specifically, the process comprises addition of bis benzene sulfonimide in an aqueous solution of chlorinating agent selected from groups of inorganic hypochlorite such as sodium hypochlorite or potassium hypochlorite or ammonium chloride or lithium chloride under stirring upto suitable time 5-30 minutes preferably 10-15 minutes. The temperature of the reaction mass is maintained at 5-30°C, preferably the temperature of the reaction mass is maintained at 15-20°C. In the reaction mass sodium bicarbonate or sodium carbonate or ammonium carbonate is slowly added while maintaining the reaction temperature at 5-30°C, preferably the temperature of the reaction mass is maintained at 15-20°C. In this reaction mass, aqueous solution of oxone was added over a period of 2 hours while maintaining temperature of reaction mass between 15-20°C. After the complete addition of aqueous solution of oxone the reaction mass was further stirred upto 60 minutes at the temperature 15-20°C. The completion of reaction was checked using techniques such as TLC, HPLC and GC. The resultant slurry was filtered and washed with water. The resultant slurry was then dried using techniques such as oven drying, drying under pressure preferably the product is dried in vacuum oven at 45°C for 5

hours. The obtained product is characterized using techniques melting point, Thin layer chromatography, Gas Chromatography, NMR, FTIR, HRMS etc. The purity of the product was checked using techniques such as by HPLC, GC, GC-MS and melting point.
For the purpose of invention bis benzene sulfonimide/substituted bis benzene sulfonimide or their salts can be used easily for the said reaction to obtain the desired product namely N-Chloro bis benzene sulfonimide/N-Chloro substitutedbis benzene sulfonimide or intermediates or polymorphs or salts thereof of general formula (I). Bis benzene sulfonimide or substituted bis benzene sulfonimide or their salts are readily available commercially or can be prepared using literature procedures. The sodium salts of Bis benzene sulfonimide can also be prepared using sodium hydroxides in water.
For the purpose of invention chlorinating agent is selected from groups of inorganic hypochlorite such as sodium hypochlorite or potassium hypochlorite or ammonium chloride or lithium chloride preferably sodium hypochlorite or potassium hypochlorite is used.
For the purpose of invention oxone is used as an aqueous solution which is prepared by dissolving the desired quantity of oxone in a desired quantity of water. Oxone is an oxidizing agent having composition 2KHSO5. KHSO4. K2SO4. Oxone as an oxidizing agent presents a good stability, simple handling, the non-toxic nature, and the low costs.
For the purpose of invention base is selected from groups of alkali or alkaline earth metal salts such as sodium bicarbonate or sodium carbonate or ammonium carbonate.

As described the product N-Chloro bis benzene sulfonimide/N-Chloro substituted bis benzene sulfonamide as prepared herein, can be characterized by various techniques such as melting point, Thin layer chromatography, Gas Chromatography, FTIR spectra, NMR spectra and GC-MS, HPLC and HRMS. Thin Layer Chromatography was done on pre-coated silica gel plates (Kiesegel 60 F254Macherey-Nagel). Gas Chromatography was performed on Shimadzu (model) with 8% OV-17 column 1.8 meter at 200°C on Isothermal mode. HPLC was performed on Agilent 1200 with C18 column in Acetonitrile: Water 20:80 ratio on isothermal mode. FTIR spectra were recorded on Thermo scientific (Nicolet IS 5). Melting point was recorded on Veego VMP-CM. HPLC was recorded on Agilent. HRMS (High Resolution Mass Spectrometry) was recorded on Shimadzu LCMS-9030 Q-TOF Mass Spectrometer by the direct infusion method.
The main advantage of the present invention is that it provides a novel process for the preparation of N-Chloro bis benzene sulfonimide/N-Chloro substituted bis benzene sulfonimide or intermediates or polymorphs or salts thereof of general formula (I) using chlorinating agent and oxone system. The process is industrial viable and uses the commercially available raw materials. Further advantage of the present invention is that it provides a novel process for the preparation of N-Chloro bis benzene sulfonimide/N-Chloro substituted bis benzene sulfonimide or intermediates or polymorphs or salts thereof of general formula (I) in quantitative yield and high purity. In contrary to prior art processes, in the invented process molecular chlorine (Cl2 gas) is not used which is hazardous because excess of chlorine is difficult to quench. Further as per prior art process as described in JP 2016204367A assigned to Nippon Soda Co., Ltd., Japan, product was not formed when sodium hypochlorite or potassium hypochlorite is used alone, the product was formed when addition of oxone was done. Further as per prior art process as described in JP 2016204367A assigned to Nippon Soda Co., Ltd., Japan, the chlorinating agent used is organic alkyl hypochlorite such as t-butyl hypochlorite and ethyl hypochlorite, since these

hypochlorites belongs to organic alkyl hypochlorites and shows good solubility in organic solvents, hence assuming that they can react directly in the solvent without any additional base or oxidant. But, we have observed that product was not formed without oxidant. Further organic hypochlorites are not stable even at room temperature, they start decomposition with hazardous gases like methyl chloride etc. Contrary to these drawbacks the present invention uses inorganic hypochlorites and oxone as oxidant and obtained the desired product in yield 90-98%.
EXAMPLES:
Example1: Preparation of N-Chloro bis benzene sulfonimide: In a 3 litre 4 necked round bottomed flask 2.1 litre sodium hypochlorite was charged. 297.0g bis benzene sulfonimide was charged in the above reaction mass and the reaction mass was stirred for 15 minutes while maintaining the reaction temperature at 15-20°C. 83.5g sodium bicarbonate was added slowly to the above reaction mass while maintaining the temperature of reaction mass at 15-20°C. In another flask 151.0g oxone was dissolved in 650 ml water. This solution of oxone was added to the reaction mass over a period of 2 hours while maintaining temperature of reaction mass between 15-20°C. After complete addition of the oxone solution the reaction mass was further stirred for 60 minutes. The obtained white slurry was filtered and washed with water. The white slurry wet cake was unloaded on glass tray and dried under vacuum oven at 45°C for 5 hours. Percentage yield: 98%. HPLC Purity: 99.58%.
HRMS (MH+): Calculated: 331.798; found: 329.062.
IR (neat) (cm-1): 3095, 2361, 1683, 1635, 1581, 1558, 1540, 1507, 1475, 1448, 1385, 1350, 1321, 1157, 1081, 1023, 998, 873, 806, 756, 748, 681, 616, 608.

Example 2: Preparation of N-Chloro bis benzene sulfonimide: In a 3 litre 4 necked round bottomed flask 2.6 litre potassium hypochlorite was charged. 297.0g bis benzene sulfonimide was charged in the above reaction mass and the reaction mass was stirred for 15 minutes while maintaining the reaction temperature at 15-20°C. To this was added 83.5g sodium bicarbonate slowly while maintaining the temperature of reaction mass to 15-20°C. In another flask 151.0g oxone was dissolved in 650 ml water. This solution of oxone was added to the reaction mass over a period of 4 hours while maintaining temperature of reaction mass between 15-20°C. After complete addition of the oxone solution the reaction mass was further stirred for 60 minutes. The obtained white slurry was filtered and washed with water. The white slurry wet cake was unloaded on glass tray and dried under vacuum oven at 45°C for 5 hours. Percentage yield: 96.8%.
Example 3: Preparation of N-Chloro bis benzene sulfonimide: In a 3 litre 4 neckedround bottomed flask 2.1 litre sodium hypochlorite was charged followed by the addition of 297.0g bis benzene sulfonimide. The reaction mass was stirred for 15 minutes while maintaining the reaction temperature at 15-20°C. To this reaction mass 95.8.5g ammonium carbonate was added slowly while maintaining the temperature of reaction mass to 15-20°C. In another flask 151.0g oxone was dissolved in 650ml water. The solution of oxone was added to the above reaction mass over a period of 2 hours while maintaining temperature of reaction mass between 15-20°C. After complete addition of the oxone solution the reaction mass was further stirred for 60 minutes. The obtained white slurry was filtered and washed with water. The white slurry wet cake was unloaded on glass tray and dried under vacuum oven at 45°C for 5 hours. Percentage yield: 90%.
Comparative Example 4: Preparation of N-Chloro bis benzene sulfonimide: In a 500ml 4 necked round bottomed flask 360.0ml sodium hypochlorite was charged. The reaction mass was cooled to 15-20°C. At this temperature bis benzene

sulfonimide 50.0g was charged slowly. The reaction mass was stirred for 4 hours. Sample was drawn from the reaction mass and filtered and dried under vacuum. The sample was analysed for chlorine content. Since after 4 hours the desired chlorine content was not obtained, so the reaction mass was further stirred for 20 hours. Similar sampling was done and chlorine content was checked. The sample showed no chorine content. This shows that product has not formed.
Comparative Example 5: Preparation of N-Chloro bis benzene sulfonimide: In a 500ml 4 necked round bottomed flask 360.0ml sodium hypochlorite was charged. The reaction mass was cooled to 15-20°C. At this temperature bis benzene sulfonimide 50.0g was charged slowly. The reaction mass was stirred for 4 hours. Sample was drawn from the reaction mass and filtered and dried under vacuum. The sample was analysed for chlorine content. Since after 4 hours the desired chlorine content was not obtained, so the reaction mass was further stirred for 20 hours. Similar sampling was done and chlorine content was checked. The sample showed no chorine content. This shows that product has not formed.
It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention with specific examples. Thus, it is intended that the present invention covers the modifications and variations of this invention that come within the scope of any claims and their equivalents. Compounds of the present invention as defined by general formula (I) may be prepared, by processes as described in foregoing non-limiting examples and description, the various modification in the above processes and examples may be applied as to obtained the desired products and which are known to person skilled in the art and usually applied during preparation of chemicals.

WE CLAIM:
1. A novel process for the preparation of N-Chloro bis benzene sulfonimide/N-
Chloro substituted bis benzene sulfonimide of formula I or intermediates or
polymorphs or salts thereof comprises the reaction of bis benzene
sulfonimide/substituted bis benzene sulfonimide with novel chlorinating agent
and oxidant system,

Wherein,
R1and R2 represents H, alkyl, alkenyl, alkynyl, cyclic alkyl haloalkyl, halogen,
nitro, hydroxy, alkoxy, alkylthio, sulfur, sulfoxy, carboxy, cyano, amide, aryl,
aralkyl, aralkenyl, alkaryl;
m and n represent an integer from 0-5.
2. The process as claimed in claim 1, wherein novel chlorinating agent and oxidant system comprises the chlorinating agent selected from sodium hypochlorite, potassium hypochlorite, ammonium chloride, lithium chloride and the like and oxidant system is oxone.
3. A novel process for the preparation of N-Chloro bis benzene sulfonimide/N-Chloro substituted bis benzene sulfonimide of formula I comprises the reaction of bis benzene sulfonimide/substituted bis benzene sulfonimide with chlorinating agent and oxone system in aqueous medium as shown in below reaction scheme:


Wherein,
R1and R2 represents H, alkyl, alkenyl, alkynyl, cyclic alkyl haloalkyl, halogen,
nitro, hydroxy, alkoxy, alkylthio, sulfur, sulfoxy, carboxy, cyano, amide, aryl,
aralkyl, aralkenyl, alkaryl;
m and n represent an integer from 0-5;
A represents the sodium hypochlorite, potassium hypochlorite, ammonium
chloride, lithium chloride; and
B represents the sodium bicarbonate, sodium carbonate, ammonium
carbonate.
4. A novel process for the preparation of N-Chloro bis benzene sulfonimide/N-Chloro substituted bis benzene sulfonimide of formula I,

comprises the steps of:
a) charging the reagent, A in reaction vessel;
b) charging the bis benzene sulfonimide or substituted bis benzene sulfonimide in a reaction vessel of step a);
c) stirring the solution of step b) for a suitable time at suitable temperature;

d) adding slowly reagent, B to the reaction mixture of step c);
e) maintaining the suitable reaction temperature of step d);
f) adding slowly the aqueous oxone solution in a reaction mass of step e);
g) maintaining the suitable reaction temperature of step f);
h) stirring the solution of step g) for a suitable time at suitable
temperature;
i) filtering the resultant mass of step h); and
j) drying the resultant mass of step i).
5. The process as claimed in claim 4, wherein in step a) reagent A is selected from sodium hypochlorite, potassium hypochlorite, ammonium chloride, lithium chloride and the like and in step d) reagent B is selected from sodium bicarbonate, sodium carbonate, ammonium carbonate and the like.
6. The process as claimed in claim 4, wherein in step c) the suitable time is 5-30 minutes preferably10-15 minutes and the suitable temperature is 5-30°C preferably 15-20°C, and in step e) and step g) the suitable temperature is 5-30°C preferably 15-20°C, and in step h) the suitable time is 40-60 minutes preferably 60 minutes and the suitable temperature is 5-30°C preferably 15-20°C.
7. A novel process for the preparation of N-Chloro bis benzene sulfonimide of formula I,


Wherein, R1and R2 represents H, comprises the reaction of bis benzene sulfonimide with novel chlorinating agent and oxidant system.
8. The process as claimed in claim 7, wherein novel chlorinating agent and oxidant system comprises the chlorinating agent selected from sodium hypochlorite, potassium hypochlorite, ammonium chloride, lithium chloride and the like and oxidant system is oxone.
9. A novel process for the preparation of N-Chloro bis benzene sulfonimide of formula I,

Wherein, R1and R2 represents H, comprises the steps of:
a) adding bis benzene sulfonimide in sodium hypochlorite solution;
b) stirring the solution of step a) for 10-15 minutes at 15-20oC;
c) adding slowly sodium bicarbonate to the reaction mixture of step b);
d) adding slowly the aqueous oxone solution in a reaction mass of step c);
e) stirring the solution of step d) for 40-60 minutes; and
f) obtaining the resultant mass.
10. A novel process for the preparation of N-Chloro bis benzene sulfonimide of
formula I,


Wherein, R1and R2 represents H, comprises the reaction of bis benzene sulfonimide with chlorinating agent sodium hypochlorite and oxone in aqueous medium and obtaining the products in 98% yield with 99.58% HPLC purity.

Documents

Application Documents

# Name Date
1 201821026753-PROVISIONAL SPECIFICATION [17-07-2018(online)].pdf 2018-07-17
2 201821026753-PROOF OF RIGHT [17-07-2018(online)].pdf 2018-07-17
3 201821026753-POWER OF AUTHORITY [17-07-2018(online)].pdf 2018-07-17
4 201821026753-FORM 1 [17-07-2018(online)].pdf 2018-07-17
5 201821026753-ORIGINAL UR 6(1A) FORM 1 & FORM 26-300718.pdf 2019-01-23
6 201821026753-DRAWING [17-07-2019(online)].pdf 2019-07-17
7 201821026753-CORRESPONDENCE-OTHERS [17-07-2019(online)].pdf 2019-07-17
8 201821026753-COMPLETE SPECIFICATION [17-07-2019(online)].pdf 2019-07-17
9 Abstract1.jpg 2021-10-18