The preparation method of 3-ethanesulfonyl-2-pyridinesulfonamide and its intermediate

A technology of ethylsulfonylpyridine and ethylsulfonyl, which is applied in the field of preparation of 3-ethylsulfonyl-2-pyridinesulfonamide and its intermediates, can solve the problems of high production cost, unsuitability for industrial production, and expensive raw materials

Active Publication Date: 2018-04-03
联化科技(上海)有限公司 +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] The technical problem to be solved by the present invention is to overcome the cumbersome reaction steps, low yield, high raw material price, high production cost and unsuitability for industrialized production in the preparation method of 3-ethanesulfonyl-2-pyridinesulfonamide in the prior art. Deficiency provides a kind of preparation method of 3-ethanesulfonyl-2-pyridinesulfonamide and its intermediate

Method used

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  • The preparation method of 3-ethanesulfonyl-2-pyridinesulfonamide and its intermediate
  • The preparation method of 3-ethanesulfonyl-2-pyridinesulfonamide and its intermediate
  • The preparation method of 3-ethanesulfonyl-2-pyridinesulfonamide and its intermediate

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Effect test

Embodiment 1

[0083] Mix 80.00g of sodium hydroxide (2.0mol) and 350g of N,N-dimethylformamide (DMF) in a reaction flask, cool down to 0-5°C, and slowly add ethyl sulfide dropwise under constant stirring DMF solution of alcohol (ethanethiol: 124.26g (2.0mol), DMF: 80g), keep the system temperature at 0-5°C during the dropwise addition. After dropping, continue to insulate and stir for 1 to 2 hours until the solid sodium hydroxide in the reaction bottle is completely dissolved. The system was heated up to 80-100°C, and the DMF solution of 2,3-dichloropyridine (2,3-dichloropyridine: 134.54g (0.91mol), DMF: 200g) was slowly added dropwise, and the temperature of the system was maintained at 80~100℃. After dropping, keep stirring for 3-5 hours, take a sample and control it. When the HPLC content of 2,3-dichloropyridine is less than 0.5%, the reaction is considered to be over.

[0084] After the solvent and low boilers were slowly removed under reduced pressure, 172.35 g of crude 2,3-diethylth...

Embodiment 2

[0086] Mix 112.22g of potassium hydroxide (2.0mol) and 350g of N,N-dimethylacetamide (DMA) in a reaction flask, then cool down to 0-5°C, and slowly add ethyl sulfide dropwise under constant stirring Alcohol DMA solution (ethanethiol: 124.26g (2.0mol), DMA: 80g), keep the system temperature at 0-5°C during the dropwise addition. After dropping, continue to insulate and stir for 1 to 2 hours until the potassium hydroxide solid in the reaction flask is completely dissolved to obtain a DMA solution of potassium ethanethiolate.

[0087] After dissolving 134.54g of 2,3-dichloropyridine (0.91mol) in 200g of DMA, the temperature of the system was raised to 80-100°C, and the DMA solution of potassium ethanethiolate prepared above was slowly added dropwise. Maintain the system temperature at 80-100°C. After dropping, keep stirring for 3-5 hours, take a sample and control it. When the HPLC content of 2,3-dichloropyridine is less than 0.5%, the reaction is considered to be over.

[0088...

Embodiment 3

[0090] After the 2,3-diethylthiopyridine (0.20mol) that 40.0g embodiment 1 prepares is dissolved in the glacial acetic acid of 80g, the mass concentration that slowly adds 100g is the hydrogen peroxide solution of 30% (the described mass concentration is Refers to the mass of hydrogen peroxide as a percentage of the total mass of hydrogen peroxide), with the slow addition of hydrogen peroxide, the system temperature gradually rises, when the system temperature rises to 75-80 ° C, about 1 / 3 of the hydrogen peroxide solution has been added dropwise. Stop the dropwise addition, and use an ice bath to cool down the system. When the system temperature drops to 70°C, continue to drop the remaining hydrogen peroxide solution, and maintain the system temperature at 70-85°C during the dropwise addition. After dripping, keep warm at 70-85°C for 4 hours, and take samples for control. At this time, the HPLC content of 2,3-diethylthiopyridine is 7%, and continue to keep warm at 70-85°C for ...

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Abstract

The invention discloses a preparation method of 3-ethylsulfonyl-2-pyridinesulfonamide and an intermediate thereof and provides a preparation method of 3-ethylsulfonyl-2-pyridinethiol. The preparation method of 3-ethylsulfonyl-2-pyridinethiol comprises the following step of carrying out nucleophilic substitution on 2,3-diethylsulfonylpyridine and a thiolation reagent in a solvent to obtain 3-ethylsulfonyl-2-pyridinethiol, wherein the thiolation reagent is a mixture of sodium sulfide and sulfur or sodium hydrosulfide. According to the preparation method disclosed by the invention, cheap 2,3-dichloropyridine is used as a raw material, the reaction step is simple, the total yield is high, and the production cost is greatly reduced; and the preparation method is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of 3-ethanesulfonyl-2-pyridinesulfonamide and its intermediate. Background technique [0002] Erimsulfuron-methyl is a sulfonylurea herbicide with high efficiency, high selectivity, post-emergence treatment and low toxicity. 3-Ethyl-2-pyridinesulfonamide is one of the key intermediates in the synthesis of DuPont's herbicide rimsulfon. [0003] Mainly contain following three kinds of synthetic methods of 3-ethanesulfonyl-2-pyridinesulfonamide at present: [0004] Using 2-fluoropyridine as a raw material, sulfonamidation was carried out by ethylthio substitution to obtain 3-ethylsulfonyl-2-pyridinesulfonamide (EP0341011); [0005] [0006] 2. Using tetramethoxypropane as raw material, 3-ethanesulfonyl-2-pyridinesulfonamide is obtained after ethanesulfonyl acetonitrile condensation, hydrogen bromide acetic acid solution ring closure, mercapto substitution, chlorine and ammonia sulfonamidation (US5107057,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/71
CPCC07D213/71
Inventor 樊小彬王海洋林行军银亮陈冬辉何俊
Owner 联化科技(上海)有限公司
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