Synthesis of sulfonylamines compounds

A technology for sulfonamides and a synthesis method is applied in the field of synthesizing sulfonamide compounds, which can solve problems such as environmental pollution and complicated processes, and achieve the effects of high chemical yield, mild reaction conditions, and ammonia saving.

Inactive Publication Date: 2009-01-14
上海药明康德新药开发有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It mainly solves the technical problems in the synthesis of existing sulfonamide compounds, especially in the synthesis of cyclopropylsulfonamide, such as complex process and environmental pollution.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] 17.3g of anhydrous THF (4.5X) and 3.86g of cyclopropanesulfonyl chloride (1.0X) were placed in a dry three-neck reaction flask (protected by a balloon), and the temperature was lowered to -10~0°C. After passing a certain amount of ammonia gas (the molar ratio of cyclopropanesulfonyl chloride to ammonia gas is 1:15), when the internal pressure of the reactor reaches 0.01-0.04Mpa, slowly raise the temperature to 20-25°C, and at 20-25°C Stirring was continued overnight. After the reaction, filter and wash the filter cake twice with 2g THF (0.5X), concentrate the filtrate under reduced pressure to obtain a light yellow solid, and reflux the wet product with 5g ethanol (1.3X) for 30-60 minutes. Cool to 0-2°C, filter, and dry the filter cake under reduced pressure at 40-50°C for 24 hours to obtain 2.81 g of white solid. [GC purity: 99.6% MS (M+1): 122; 1 HNMR (400 MHz MeOD): δ 2.547-2.611 (M, 1H), 0.948-1.079 (M, 4H).

Embodiment 2

[0017] Place 173g of anhydrous THF (4.5X) and 38.6g of cyclopropanesulfonyl chloride (1.0X) in a dry high-pressure reaction flask, lower the temperature to -10 to 0°C, and feed ammonia gas until the inner pressure of the reaction flask is 0.04~0.06MPa. Slowly raise the temperature to 5~20°C, and the internal pressure of the reaction bottle to 0.4~0.6MPa. Stirring was continued overnight at 20-25°C. After the reaction was finished, filter, and the filter cake was washed twice with 15g THF (0.4X), and the filtrate was concentrated under reduced pressure to obtain a light yellow solid, and the wet product was refluxed with 50g ethanol (1.3X) for 30-60 minutes. Cool to 0-2°C, filter, and dry the filter cake under reduced pressure at 40-50°C for 24 hours to obtain 28.7 g of white solid

Embodiment 3

[0019] Put 173g of acetonitrile (4.5X) and 38.6g of cyclopropanesulfonyl chloride (1.0X) in a dry high-pressure reaction bottle, lower the temperature to -10~0°C, and feed ammonia gas until the inner pressure of the reaction bottle is 0.04~ 0.06MPa. Slowly raise the temperature to 5~20°C, and the internal pressure of the reaction bottle to 0.4~0.6MPa. Stirring was continued overnight at 20-25°C. After the reaction was finished, filter, the filter cake was washed twice with 15g acetonitrile (0.4X), the filtrate was concentrated under reduced pressure to obtain a light yellow solid, and the wet product was refluxed with 50g ethanol (1.3X) for 30-60 minutes. Cool to 0-2°C, filter, and dry the filter cake under reduced pressure at 40-50°C for 24 hours to obtain 29 g of white solid.

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Abstract

The invention relates to a synthetic method of a sulfonamide compound, The process of the invention comprises: taking a sulfochloride compound as a raw material, firstly dissolving the sulfochloride compound into an organic solvent, beginning to input an ammonia gas at a temperature of between -10 and 0 DEG C, and raising the decomposition temperature to the room temperature when the internal pressure in a reaction kettle reaches 0.01 to 0.04Mpa, by now the internal pressure in the reaction kettle increases to 0.1 to 0.6Mpa. After the reaction for 1 to 20h, the target product is acquired through filtration and recrystallization in an alcohols solvent. The synthetic method changes the feeding sequence of materials, and saves mass ammonia gas and overcomes the defects of complex operation, large consumption of ammonia gas and environmental pollution of the existing method, and the synthetic method of the sulfonamide compound has advantages of simple operation, mild reaction conditions, rather high chemical yield and low cost, and is suitable for the industrialized production.

Description

Technical field: [0001] The invention relates to a synthesis method of sulfonamide compounds. Background technique: [0002] Sulfa drugs are a class of synthetic anti-infective drugs with large production volume and various varieties. As early as 1908, the German chemist Gelmo first synthesized p-aminobenzenesulfonamide, and then a large number of sulfonamide anti-infectives were synthesized, and cyclamate was an important component of many other pharmaceutical intermediates. The synthesis of cyclopropylsulfonamide is generally to drop the tetrahydrofuran solution of cyclopropylsulfonyl chloride into the tetrahydrofuran solution of ammonia gas, and keep the ammonia gas flow for a long time. This method is complicated to operate, requires a large amount of ammonia gas, and pollutes the environment. Invention content: [0003] The purpose of the present invention is to provide a kind of can save a large amount of ammonia gas, and reaction condition is mild, and operation is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/38C07C311/14C07C311/15C07C311/02
Inventor 卢亚兵杨小根胡伟峰顾虹唐苏翰李革
Owner 上海药明康德新药开发有限公司
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