Preparation method for N-(2- chlorine-4-phenyl)-4- chlorine-3-trifluoromethyl benzene sulfonamide

A technology of trifluoromethylbenzenesulfonamide and trifluoromethylbenzenesulfonyl chloride is applied in the field of preparation of N--4-chloro-3-trifluoromethylbenzenesulfonamide, which can solve the problem of high reaction temperature and production safety There are many hidden dangers, not being used, etc., to achieve the effect of increasing the reaction yield, reducing production risks, and improving the production process

Inactive Publication Date: 2012-06-13
天津均凯农业科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This synthetic route has: (1) high reaction temperature, high energy consumption, many production safety hazards, and runs counter to the low-carbon economy advocated by the state; (2) the method of obtaining products by column chromatography is generally not used in the industrialization process

Method used

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  • Preparation method for N-(2- chlorine-4-phenyl)-4- chlorine-3-trifluoromethyl benzene sulfonamide
  • Preparation method for N-(2- chlorine-4-phenyl)-4- chlorine-3-trifluoromethyl benzene sulfonamide
  • Preparation method for N-(2- chlorine-4-phenyl)-4- chlorine-3-trifluoromethyl benzene sulfonamide

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Experimental program
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Effect test

Embodiment 1

[0029] 1.27 kilograms of o-chloroaniline and 100 grams of 4-dimethylaminopyridine were dissolved in 10 L of toluene, and the temperature was controlled at 50° C., and 2.87 kilograms of 4-chloro-3-trifluoromethylbenzenesulfonyl chloride was added dropwise. After the addition, 50 °C for 5 hours. Cooling, filtration, the filtrate recovered 8L of toluene, cooling, filtration, and ethanol recrystallization to obtain 2.52 kg of N-(2-chloro-4-phenyl)-4-chloro-3-trifluoromethylbenzenesulfonamide, yield 68 %.

Embodiment 2

[0031] 1.27 kg of o-chloroaniline and 100 g of 4-dimethylaminopyridine were dissolved in 6L of 1,2-dichloroethane, the temperature was controlled at 50°C, and 2.87 kg of 4-chloro-3-trifluoromethylbenzenesulfonyl chloride was added dropwise , After the dropwise addition was completed, the reaction was carried out at 50° C. for 5 hours. Cool, recover 4.5L of 1,2-dichloroethane, cool, filter, and recrystallize from ethanol to obtain N-(2-chloro-4-phenyl)-4-chloro-3-trifluoromethylbenzenesulfonamide 3.18 kg, yield 86%.

Embodiment 3

[0033] 1.27 kilograms of o-chloroaniline and 100 grams of 4-dimethylaminopyridine were dissolved in 14L of chlorobenzene, and the temperature was controlled at 50° C., and 2.87 kilograms of 4-chloro-3-trifluoromethylbenzenesulfonyl chloride was added dropwise. After the dropwise addition, React at 50°C for 5 hours. Cooling, filtration, filtrate reclaims 11L of chlorobenzene, cooling, filtration, ethanol recrystallization, obtains 2.66 kilograms of N-(2-chloro-4-phenyl)-4-chloro-3-trifluoromethylbenzenesulfonamide, yield 72%.

[0034] The second part: the preparation of sulfanil

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Abstract

The invention discloses a preparation method for N-(2- chlorine-4-phenyl)-4- chlorine-3-trifluoromethyl benzene sulphonamide. The preparation method is as follows: performing amino sulfonylation reaction to 4 - chlorine-3-trifluoromethyl benzene sulfonyl chloride and o-chloroaniline in the toluene solution in the presence of catalyst to acquire N-(2- chlorine-4-phenyl)-4- chlorine-3-trifluoromethyl benzene sulphonamide; and then, performing nitratlon reaction in the presence of nitric acid/sulphuric acid to acquire flusulfamide with the product purity more than 99%. The preparation method improves the reaction yield, reduces the production danger, and improves the production process on the basis of improving the reaction yield.

Description

technical field [0001] The invention belongs to a new process route for the preparation of the pesticide fungicide-sulfanil. Particularly relate to a kind of preparation method of N-(2-chloro-4-phenyl)-4-chloro-3-trifluoromethylbenzenesulfonamide Background technique [0002] Sulfanil is a new soil fungicide developed by Japan Mitsui Topress Chemical Company in 1986. The agent has a remarkable effect on cabbage clubroot, and in vitro tests have found that it also has high bactericidal activity against other crop pathogens. Sulfuramide is used as a soil fungicide and is considered safe with little impact on the environment. The chemical name of sulfanil is N-(2-chloro-4-nitrophenyl)-4-chloro-3-trifluoromethylbenzenesulfonamide (I). [0003] [0004] The preparation method of Sulfuramide is currently reported in U.S. Patent 4870107, in o-xylene solution, 4-chloro-3-trifluoromethylbenzenesulfonyl chloride and 2-chloro-4-nitroaniline in the presence of pyridine at 140- Re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/21C07C303/40
Inventor 尚振华栗晓东张慧丽
Owner 天津均凯农业科技有限公司
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