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Method for producing 1,2-enzisothiazol-3-one compound

A technology of benzisothiazole and ketone compounds, applied in the direction of organic chemical methods, chemical instruments and methods, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problems of increasing waste water and undesired needs

Inactive Publication Date: 2013-12-11
SUMITOMO SEIKA CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, in this method, harmful alkyl halides are produced during the reaction and need to be removed
This requires a detoxification system and increases waste water, etc., thus making it undesirable from an environmental and / or economic standpoint

Method used

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  • Method for producing 1,2-enzisothiazol-3-one compound
  • Method for producing 1,2-enzisothiazol-3-one compound
  • Method for producing 1,2-enzisothiazol-3-one compound

Examples

Experimental program
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Effect test

Embodiment 1

[0134] (i) Synthesis of methyl mercaptan

[0135] A 20% aqueous solution (280 g) of sodium hydrosulfide (1.00 mol), chlorobenzene (200 g), and a 50% by weight aqueous solution (3.2 g) of tetra-n-butylammonium bromide were placed under a nitrogen atmosphere equipped with a stirrer, In a 500mL four-necked flask with a thermometer, a condenser and a gas blow tube. The mixture was stirred at 30°C.

[0136] 2-(Methylthio)benzonitrile (298.0 g, 2.0 moles), monochlorobenzene (460.0 g) and 35% by weight hydrochloric acid (67.0 g, hydrochloric acid: 0.6 moles, water: 2.4 moles) were placed in a stirrer equipped with , a thermometer and a condenser in a 3L four-necked flask. Sulfonyl chloride (270.0 g, 2.0 mol) was added thereto while stirring at 5°C to 15°C. The mixture was further heated to 65-70°C and allowed to react for 1 hour. Gas generated during the reaction was passed through 15% aqueous sodium hydroxide to remove hydrogen chloride. The obtained methyl chloride gas (50.5...

Embodiment 2

[0145] (i) Synthesis of ethanethiol

[0146] Under a nitrogen atmosphere, a 20% aqueous solution (280 g) of sodium hydrosulfide (1.00 mol), chlorobenzene (100 g) and a 50% by weight aqueous solution (3.2 g) of tetra-n-butylammonium bromide were placed in a device equipped with a stirrer, a thermometer, , condenser and blow tube in a 500mL four-necked flask. The mixture was stirred at 30°C.

[0147] 2-(Ethylthio)benzonitrile (326.0 g, 2.0 moles), monochlorobenzene (460.0 g) and 35% by weight hydrochloric acid (67.0 g, hydrochloric acid: 0.6 moles, water: 2.4 moles) were placed in a stirrer equipped with , a thermometer and a condenser in a 3L four-necked flask. While stirring, chlorine gas (156.0 g, 2.2 mol) was blown thereinto at 45°C˜50°C over 2 hours, and the resulting mixture was further heated to 65°C˜70°C and then allowed to react for 1 hour. Gas generated during the reaction was passed through 15% aqueous sodium hydroxide to remove hydrogen chloride. The resulting ...

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Abstract

The present invention provides a method for producing a 1,2-benzisothiazol-3-one compound whereby the alkyl halide by-product that is generated when a 2-(alkylthio)benzonitrile compound and a halogenation agent are reacted in the presence of water is reacted with a sulfide to become an alkylthiol and then, as an alkali metal salt, is reacted with a 2-halobenzonitrile compound in order to be converted to a 2-(alkylthio)benzonitrile compound and reused as a starting material for the production of a 1,2-benzisothiazol-3-one compound. By means of the present invention, it is possible to efficiently use the by-product that is generated during the production of a 1,2-benzisothiazol-3-one compound and economically produce a 1,2-benzisothiazol-3-one compound without placing a burden on the environment.

Description

technical field [0001] The present invention relates to a method for producing 1,2-benzisothiazol-3-one compounds useful as antibacterial agents, antifungal agents, and the like. Background technique [0002] As an example of a known method for producing a 1,2-benzisothiazol-3-one compound, a 2-(alkylthio)benzonitrile compound is reacted with a halogenating agent in the presence of water (Patent Document 1). [0003] However, in this method, harmful alkyl halides are produced during the reaction and need to be removed. This requires a detoxification system and increases waste water etc., thus making it undesirable from an environmental and / or economic standpoint. [0004] prior art literature [0005] patent documents [0006] Patent Document 1: Japanese Patent Application Laid-Open No. 8-134051 Contents of the invention [0007] technical problem [0008] The present invention has been accomplished in view of the above-mentioned disadvantages of the prior art. The m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D275/04B01J31/02C07C319/14C07C323/62C07B61/00
CPCC07C319/14C07C319/02Y02P20/582C07D275/04C07C323/62C07C321/04B01J31/02C07C319/12
Inventor 神田尚明小西博嗣山口弘贵
Owner SUMITOMO SEIKA CHEM CO LTD
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