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Preparation method of 3-isothiazolinone compound

A technology for isothiazolinones and compounds, which is applied in the field of preparation of 3-isothiazolinone compounds, can solve the problems of intermediate conversion, chlorination reagent consumption, overall yield reduction, etc., and achieve yield improvement and economic benefits Significant, cost-increasing effect

Pending Publication Date: 2020-12-22
DALIAN BIO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Water or alcohol in the reaction system will not only quench free radicals, resulting in excessive consumption of chlorinated reagents, but also cause conversion of intermediates to by-products, resulting in a decrease in overall yield

Method used

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  • Preparation method of 3-isothiazolinone compound
  • Preparation method of 3-isothiazolinone compound
  • Preparation method of 3-isothiazolinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] A kind of preparation method of 3-isothiazolinone compound, concrete steps are as follows:

[0032] Add 200g of ethyl acetate and 23.6g (0.1mol) of N,N'-dimethyl-3,3'-dithiodipropionamide into a 500ml four-necked bottle equipped with a thermometer and a stirrer, stir and mix, and control The reaction temperature was 15°C, and 1.8 g of thionyl chloride (15.1 mmol) was added into a four-necked flask, and stirred for 10 min to mix. Feed 21.3g (0.3mol) of chlorine gas into the reaction system, stir the mixture for 5h to react, filter and separate to obtain 27.1g of the product, test the external standard content of N-methyl-3-isothiazolinone (MIT) to be 72.1%, and the yield 84.9%. See HPLC spectrum figure 1 , MIT retention time is about 2.3min.

Embodiment 2

[0034] A kind of preparation method of 3-isothiazolinone compound, concrete steps are as follows:

[0035] Add 200 g of dichloroethane and 23.8 g (0.2 mol) of N-methyl-mercaptopropionamide into a 500 ml four-necked bottle equipped with a thermometer and a stirrer, stir and mix, control the temperature of the reaction system at 5°C, and add 0.30 g of oxytrichloride Phosphorus (1.96mmol) was added into the four-necked flask, and stirred for 50min to mix. 31.9 g (0.45 mol) of chlorine gas was passed into the reaction system, the mixture was stirred for 2 h to react, and 31.4 g of the product was obtained by filtration and separation. The MIT+CIT external standard content was 73.1%, and the yield was 81.5%.

Embodiment 3-7

[0037] Embodiment 3-7 is based on different substituents (R 1 ) of dithiodipropionamide (0.1mol) is a raw material, the tests carried out under conditions such as different temperatures, dehydrating agents, solvents, the results are shown in Table 1:

[0038] Table 1

[0039]

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Abstract

The invention discloses a preparation method of a 3-isothiazolinone compound, which comprises the following steps of adding raw materials and a solvent into a reaction system, and stirring and mixing,adding a dehydrating agent into the mixed solution, and stirring for reaction, introducing chlorine into the reaction system, stirring the reaction mixture for reaction, filtering and separating to obtain a product. According to the method, the chemical dehydrating agent is added into the reaction system to react with water or alcohol in the reaction system, so that water or alcohol in the systemis removed, side reaction caused by water or alcohol is avoided, the reaction yield is increased, and the economic benefit is remarkable.

Description

technical field [0001] The invention relates to a preparation method of 3-isothiazolinone compounds, belonging to the technical field of chemical industry. Background technique [0002] 3-isothiazolinone compounds (chemical structure such as formula I) are a class of broad-spectrum fungicides, which have the advantages of high efficiency, broad-spectrum, low toxicity, harmless under the use concentration, and can be naturally degraded in the environment. They are widely used in Industrial water treatment, cosmetics, building materials, coatings, medical and health, textiles, photography, detergents and other fields. [0003] [0004] R in Formula I 1 = alkyl; R 2 , R 3 =H or Cl. [0005] There are many synthetic routes for 3-isothiazolinone compounds, but the main preparation route is based on three U.S. patent applications submitted by Rohm and Haas in 1967 (application numbers are US621766, US621770, and US621780). Lai (Li Shichang, Yang Yunong, Zhang Gongmin, et a...

Claims

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Application Information

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IPC IPC(8): C07D275/03
CPCC07D275/03
Inventor 杨兆辉强新新李振宇张晓娜刘述宽贾儒刘伟顾振鹏
Owner DALIAN BIO CHEM
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