Preparation method of 3-ethylsulfonyl-2-pyridinesulfonamide and intermediate thereof

A technology of ethylsulfonylpyridine and ethylsulfonyl, which is applied in the field of preparation of 3-ethylsulfonyl-2-pyridinesulfonamide and intermediates thereof, can solve the problems of unsuitability for industrialized production, low yield, expensive raw materials and the like

Active Publication Date: 2015-12-16
联化科技(上海)有限公司 +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] After mixing 80.00g of sodium hydroxide (2.0mol) and 350g of N,N-dimethylformamide (DMF) in the reaction flask, the temperature is lowered to 0~5℃, and ethyl sulfide is slowly added dropwise under constant stirring. DMF solution of alcohol (ethanethiol: 124.26 g (2.0 mol), DMF: 80 g), keep the temperature of the system at 0-5°C during the dropping process. After dripping, continue to heat and stir for 1 to 2 hours until the solid sodium hydroxide in the reaction flask is completely dissolved. The temperature of the system was raised 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 during the dropping process. 80~100℃. After dripping, keep agitating for 3 to 5 hours, and control sampling. When the HPLC content of 2,3-dichloropyridine is less than 0.5%, the reaction is considered to be complete.

[0084] After slowly removing the solvent...

Embodiment 2

[0086] After mixing 112.22g potassium hydroxide (2.0mol) and 350g N,N-dimethylacetamide (DMA) in the reaction flask, the temperature is reduced to 0~5℃, and ethyl sulfide is slowly added dropwise under constant stirring. Alcohol DMA solution (ethanethiol: 124.26 g (2.0 mol), DMA: 80 g), keep the temperature of the system at 0-5°C during the dropping process. After dripping, continue to heat 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 134.54g of 2,3-dichloropyridine (0.91mol) was dissolved 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 temperature of the system at 80-100°C. After dripping, keep agitating for 3 to 5 hours, and control sampling. When the HPLC content of 2,3-dichloropyridine is less than 0.5%, the reaction is c...

Embodiment 3

[0090] After 40.0g of 2,3-diethylthiopyridine (0.20mol) prepared in Example 1 was dissolved in 80g of glacial acetic acid, 100g of hydrogen peroxide solution with a mass concentration of 30% (the mass concentration is It refers to the percentage of the mass of hydrogen peroxide in the total mass of hydrogen peroxide). With the slow addition of hydrogen peroxide, the temperature of the system gradually rises. When the temperature of the system rises to 75-80°C, about 1 / 3 of the hydrogen peroxide solution has been added dropwise. Stop the dripping and use an ice bath to cool the system. When the temperature of the system drops to 70°C, continue to drip the remaining hydrogen peroxide solution, and maintain the system temperature at 70-85°C during the dripping process. After dripping, keep the temperature at 70~85℃ for 4 hours, and control the sampling. At this time, the HPLC content of 2,3-diethylthiopyridine is 7%. Continue to keep at 70~85℃ for 1 hour, 2,3-diethylsulfide The HP...

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PUM

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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 intermediates. Background technique [0002] Immersulfuron is a sulfonylurea herbicide with high efficiency, high selectivity and low toxicity in post-emergence treatment. 3-ethanesulfonyl-2-pyridinesulfonamide is one of the key intermediates for the synthesis of DuPont's herbicide rimsulfon. [0003] At present, there are mainly three synthetic methods of 3-ethanesulfonyl-2-pyridinesulfonamide as follows: [0004] Using 2-fluoropyridine as a raw material, the ethylthio group is substituted and then sulfonated to obtain 3-ethanesulfonyl-2-pyridinesulfonamide (EP0341011); [0005] [0006] 2. Using tetramethoxypropane as the raw material, after ethanesulfonyl acetonitrile condensation, hydrogen bromide acetic acid solution ring closure, sulfhydryl substitution, chlorine and sulfonamide sulfonamide to obtain 3-ethanesulfonyl-2-pyridinesulfonamide (US5107057, Modern Pe...

Claims

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Application Information

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Patent Type & Authority Applications(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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