Synthesis method of chesulfamide

The technology of a cyclohexasulfame and its synthesis method is applied in the direction of sulfonamide preparation, sulfonate preparation, organic chemistry, etc. It can solve the problems of difficult operation, many wastes in the synthesis technology, harsh conditions, etc., and achieves mild process conditions, The effect of reducing the discharge of three wastes and simple operation

Active Publication Date: 2019-10-18
CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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Problems solved by technology

[0005] The purpose of the present invention is to provide a high-yield, easy-to-operate, environmentally friendly new technology for synthesizing cyclohexasulfame, which overcomes the defects of existing cyclohexasulfame synthesis technology with many wastes, difficult operation and harsh conditions

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  • Synthesis method of chesulfamide
  • Synthesis method of chesulfamide
  • Synthesis method of chesulfamide

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Embodiment

[0032] In the present invention, the specific synthetic method of cyclohexasulfame can be decomposed into following 3 technological engineerings:

[0033] (1) Preparation of sodium 2-oxocyclohexylsulfonate

[0034] 13.26 g (100 mmol) of 2-chlorocyclohexanone, 18.91 g (150 mmol) of anhydrous sodium sulfite and 300 ml of water were mixed and charged into a 500 ml round-bottomed flask, and stirred at reflux at 100°C for 20 hours. After the reaction is complete, when the reaction liquid is cooled to about 40°C, the solvent is rotovapped to dryness. Add 500ml of absolute ethanol to the raffinate, evaporate the remaining water to dryness, add 200ml of 1:1 anhydrous ether-n-hexane, stir at room temperature for a period of time, filter with suction, and dry under reduced pressure to obtain 2-oxocyclohexyl The crude sodium sulfonate was directly used in the next reaction.

[0035] (2) Preparation of 2-oxocyclohexylsulfonyl chloride

[0036] Add sodium 2-oxocyclohexylsulfonate obtain...

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Abstract

The invention provides a synthesis method of chesulfamide. The method includes the steps of: reacting the halogenation product 2-halogenated cyclohexanone of cyclohexanone with sulfite to obtain 2-cyclohexylsulfonate; then carrying out reaction with oxalyl chloride, 2-trifluoromethyl-4-chloroaniline to obtain chesulfamide. In the invention, 2-halogenated cyclohexanone and sulfite are employed to substitute cyclohexanone and sulfur trioxide.1, 4-dioxane compound, thus avoiding the problems that the end point of chemical reaction for removal of SO4<2-> with precipitant BaCl2 or Ba(OH)2 is hardlycontrollable and the generated BaSO4 precipitate cannot be utilized and become three wastes, and overcoming the disadvantages of corrosion, difficult storage, difficult operation, strong irritating odor, easy cause of poisoning and the like of ammonia gas. The method provided by the invention has the advantages of mild reaction conditions, simple operation, high product purity and high yield, andis suitable for large-scale industrial application.

Description

technical field [0001] The present invention relates to a chemical synthesis technology of the compound N-(2-trifluoromethyl-4-chlorophenyl)-2-oxocyclohexylsulfonamide (abbreviated as cyclohexasulfame in the present invention) in the field of agricultural chemistry . Background technique [0002] Cyclohexasulfame is a new fungicide discovered by China Agricultural University in 2004. It can be used to prevent and control various crop diseases such as tomato gray mold, rape sclerotinia, cucumber brown spot, and scab. The general molecular structure formula and compound technology of its series of compounds are disclosed in the patent application number 200510085408.4 "2-oxocycloalkylsulfonamide, its preparation method and use as a fungicide". In this invention, cyclohexanone is used as raw material to synthesize 2-oxocyclohexylsulfonate potassium salt intermediate firstly, and after the latter obtains 2-oxocyclohexylsulfonyl chloride with oxalyl chloride, it is mixed with 2-...

Claims

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Application Information

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IPC IPC(8): C07C303/38C07C311/14
CPCC07C303/32C07C303/38C07C2601/14C07C311/14C07C309/25
Inventor 李江胜陈超姜思杨盼盼谢欣芸李志伟
Owner CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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