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Preparation method of 2-n-octyl-4-bromo-5-chloro-3-isothiazolone

A technology of isothiazolone and n-octylpropionamide, applied in the direction of organic chemistry, etc., can solve the problems such as no suitable method for 2-n-octyl-4-bromo-5-chloro-3-isothiazolone, and achieve Conducive to separation and purification, simple synthesis, and accurate position positioning

Inactive Publication Date: 2016-02-03
DALIAN JOIN KING FINE CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the existing methods of synthesizing 4,5-dichloro-2-n-octyl-3-isothiazolinone, the impurity 2-n-octyl-4-bromo-5-chloro-3-isothiazolinone will inevitably be generated For thiazolone, in order to carry out accurate qualitative and quantitative analysis of this impurity, on the basis of extensive literature research, there is no suitable method for preparing 2-n-octyl-4-bromo-5-chloro-3-isothiazolone, Thereby need to develop a kind of synthetic route of preparing this compound

Method used

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  • Preparation method of 2-n-octyl-4-bromo-5-chloro-3-isothiazolone
  • Preparation method of 2-n-octyl-4-bromo-5-chloro-3-isothiazolone
  • Preparation method of 2-n-octyl-4-bromo-5-chloro-3-isothiazolone

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Embodiment 1

[0032] Example 1 (sulfonyl chloride, bromine cyclization)

[0033] This example is the preparation method of 2-n-octyl-4-bromo-5-chloro-3-isothiazolone, according to the following reaction formula:

[0034]

[0035] The specific experiment process is as follows:

[0036] Add 25g (0.11mol, 96%, 1eq) of newly prepared 3-mercapto-N-n-octylpropionamide into a 250mL four-neck reactor equipped with mechanical stirring, reflux condenser and tail gas alkali absorption device, 1, 100g of 2-dichloroethane, start to heat up to 35~40℃ under the protection of nitrogen, add sulfonyl chloride 54g (0.4mol, 99%, 3.6eq) dropwise with stirring, after the dropwise addition, react for 0.5~1h, then start dropping Bromine 32g (0.2mol, 99%, 2.5eq), the system has obvious color changes during the dripping process, after the dripping is completed, the reaction is kept for 2.5~3h, sampling and analysis, the product 2-n-octyl-4-bromo-5 -Chloro-3-isothiazolone GC content is 55%, the main impurity of the system...

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Abstract

The invention discloses a preparation method of 2-n-octyl-4-bromo-5-chloro-3-isothiazolone, and belongs to the technical field of organic chemistry. According to the preparation method, 3-mercapto-N-n-octylpropionamide, sulfonyl chloride, and bromine are taken as the raw materials, 1, 2-dichloroethane is taken as the solvent, the raw materials are heated to carry out chlorine cyclization and bromination reactions to generate a mixture composed of 2-n-octyl-4-bromo-5-chloro-3-isothiazolone, 2-n-octyl-4,5-dichloro-3-isothiazolone, and other impurities, then the mixture is subjected to recrystallization and column chromatography to obtain pure 2-n-octyl-4-bromo-5-chloro-3-isothiazolone, and the yield is 35 to 43%. The provided preparation method overcomes the shortages of conventional synthesis technology. A novel synthesis method of 2-n-octyl-4-bromo-5-chloro-3-isothiazolone is provided.

Description

Technical field [0001] The invention relates to a preparation method of 2-n-octyl-4-bromo-5-chloro-3-isothiazolone, which belongs to the field of fine chemical intermediates. Background technique [0002] 4,5-Dichloro-2-n-octyl-3-isothiazolinone is recognized as a dry film antifungal agent, mainly used in plastic leather, paint, coating, sewage, paper, wood and other fields, and can also be used In adhesives, inks. It is easily compatible with water and solvents, and can be added in the first stage before dispersion. And the isothiazolinone shows good stability in ionic surfactants and emulsions. [0003] In the existing synthesis of 4,5-dichloro-2-n-octyl-3-isothiazolinone, impurity 2-n-octyl-4-bromo-5-chloro-3-iso will inevitably be generated For thiazolone, in order to carry out accurate qualitative and quantitative analysis of this impurity, on the basis of extensive literature research, there is no suitable method for preparing 2-n-octyl-4-bromo-5-chloro-3-isothiazolone. T...

Claims

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Application Information

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IPC IPC(8): C07D275/03
CPCC07D275/03
Inventor 宫本海李雨王荣良于斌孙晓君
Owner DALIAN JOIN KING FINE CHEM CO LTD