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Method for preparing 2-(trifluoromethoxy) benzene sulfonamide

A technology of trifluoromethoxyl and benzenesulfonamide, which is applied in the field of preparation of 2-benzenesulfonamide, can solve the problems affecting the quality of the final product, low product yield, ammonia gas harming the environment and human health, and achieves a feasible process , high product purity, good environmental effect

Inactive Publication Date: 2015-07-22
DALIAN QIKAI MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In order to solve the problems of the production process of 2-(trifluoromethoxy)benzenesulfonamide in the prior art, intermediate impurities affect the quality of the final product, ammonia gas is harmful to the environment and human health, and the product yield is low. The invention provides a preparation method with stable and easy-to-obtain raw materials, fundamentally improved operating environment in the ammoniation process, no ammonia nitrogen waste water, high product yield and low cost

Method used

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  • Method for preparing 2-(trifluoromethoxy) benzene sulfonamide
  • Method for preparing 2-(trifluoromethoxy) benzene sulfonamide

Examples

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Effect test

Embodiment 1

[0049] 1. The preparation of 2-(trifluoromethoxy)aniline hydrochloride:

[0050] In a 1000mL four-necked flask, add 200g (1.92mol) of hydrochloric acid, 100g (0.565mol) of o-amino(trifluoromethoxy)benzene and 80g of water in sequence at room temperature, stir for 1 hour, and control the reaction temperature at 0-30°C. 380 g of a salt-forming reaction solution containing 2-(trifluoromethoxy)aniline hydrochloride was obtained.

[0051] ② Preparation of 2-(trifluoromethoxy)benzenediazonium salt:

[0052] Under stirring, add 120g (0.579mol) sodium nitrite aqueous solution dropwise to the 380g salt-forming reaction solution obtained in step ①, the reaction temperature is controlled at -20~5°C, the dropwise addition is completed in 1h, and the temperature is kept for 1h to obtain 500g of sodium nitrite containing 2 -Diazotization reaction solution of (trifluoromethoxy)benzene diazonium salt.

[0053] ③The preparation of 2-(trifluoromethoxy)benzenesulfonyl chloride:

[0054] In a ...

Embodiment 2

[0059] 1. The preparation of 2-(trifluoromethoxy) aniline sulfate:

[0060] In a 1000mL four-necked flask, add 62.2g (0.622mol) of concentrated sulfuric acid, 100g (0.565mol) of o-amino(trifluoromethoxy)benzene and 100g of water in turn at room temperature, stir for 1 hour, and control the reaction temperature at 80-100 °C, 262 g of a salt-forming reaction solution containing 2-(trifluoromethoxy)aniline sulfate was obtained.

[0061] ② Preparation of 2-(trifluoromethoxy)benzenediazonium salt:

[0062] Under stirring, add 385g (0.678mol) potassium nitrite aqueous solution dropwise to the 262g salt-forming reaction solution obtained in step ①, the reaction temperature is controlled at 40-50°C, the dropwise addition is completed in 3h, and the temperature is kept for 1h to obtain 646g The diazotization reaction solution of (trifluoromethoxy)benzene diazonium salt.

[0063] ③The preparation of 2-(trifluoromethoxy)benzenesulfonyl chloride:

[0064] In a 2000mL four-neck bottle, ...

Embodiment 3

[0068] 1. Preparation of 2-(trifluoromethoxy)aniline phosphate:

[0069] In a 1000mL four-neck flask, add 651g (5.65mol) of phosphoric acid and 100g (0.565mol) of o-amino(trifluoromethoxy)benzene at room temperature, and stir for 1 hour. The reaction temperature is controlled at 50-60°C to obtain 750g of Salt-forming reaction solution of 2-(trifluoromethoxy)aniline sulfate.

[0070] ② Preparation of 2-(trifluoromethoxy)benzenediazonium salt:

[0071] Under stirring, add 117g (0.566mol) sodium nitrite aqueous solution dropwise to the 750g salt-forming reaction solution obtained in step ①, the reaction temperature is controlled at 45-50°C, the dropwise addition is completed in 2h, and the temperature is kept for 1h to obtain 867g containing 2- The diazotization reaction solution of (trifluoromethoxy)benzene diazonium salt.

[0072] ③The preparation of 2-(trifluoromethoxy)benzenesulfonyl chloride:

[0073] In a 2000mL four-necked bottle, add 117g (1.13mol) of hydrochloric acid...

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Abstract

The invention provides a method for preparing 2-(trifluoromethoxy) benzene sulfonamide. The method comprises the following steps: taking o-amino (trifluoromethoxy) benzene as a raw material, generating salt forming reaction with inorganic acid, then generating diazo-reaction with nitrite, and finally generating chlorosulfonation reaction under the condition of coexistence of a cupric compound, sulfite and hydrochloric acid; enabling the product to generate aminating reaction with ammonium salt and strong base to prepare 2-(trifluoromethoxy) benzene sulfonamide. The raw materials used by the method are easily obtained and can be purchased in China. The method has the advantages of being simple in process, convenient to operate, high in product purity (larger than or equal to 99 percent), low in cost, safe and efficient, saving energy and reducing consumption, thereby being more suitable for industrialized mass production.

Description

technical field [0001] The invention relates to a preparation method of 2-(trifluoromethoxy)benzenesulfonamide, which belongs to the field of organic synthesis. Background technique [0002] 2-(trifluoromethoxy)benzenesulfonamide product is a very important organic intermediate, currently mainly used in the production of 2-(trifluoromethoxy)benzenesulfonyl isocyanate, which is an important part of the production of sulfonylurea drugs raw material. So far, only CN101671284A discloses its preparation method relatively completely, through (1) salt formation and diazotization: throw 100 parts of 35% hydrochloric acid in the bottle, drop o-trifluoromethoxyaniline, add water 100 60 parts of sodium nitrite aqueous solution prepared in advance was added dropwise between -5 and 5°C, and kept for 1 hour after the addition; (2) Synthesis: put 200 parts of hydrochloric acid into the bottle, catalyst FeCl 3 5 parts, cool down to 0°C, add NaHSO 3 40 parts, and then drop the produced di...

Claims

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Application Information

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IPC IPC(8): C07C303/38C07C311/29
Inventor 侯光姜殿平
Owner DALIAN QIKAI MEDICAL TECH
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