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Method for synthesizing sulfonylureas compound under phase-transfer catalysis

A technology of phase-transfer catalysis and phase-transfer catalyst, which is applied in the field of synthesis of sulfonylurea compounds, can solve the problems of many steps, high production costs, and expensive raw materials, and achieve the effects of increasing yield, easy operation, and reducing costs

Inactive Publication Date: 2012-03-21
NANJING HUAZHOU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are many steps in these methods, the yield is not high, and the raw materials are expensive, so the production cost is relatively high.

Method used

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  • Method for synthesizing sulfonylureas compound under phase-transfer catalysis
  • Method for synthesizing sulfonylureas compound under phase-transfer catalysis

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Example 1: Preparation of 2-(4,6-dichloropyrimidin-2-yl)-1-(2-methoxycarbonylbenzene-1-yl)sulfonylurea

[0023] Weigh 23.4g of 2-methoxycarbonyl-1-benzenesulfonyl chloride into the reactor, add 100mL of acetonitrile, then weigh 6.6g of NaOCN, add 0.8g of n-butylammonium bromide into the reaction solution, stir at room temperature for 1.5 After 1 h, add 16.4 g of 4,6-dichloro-2-aminopyrimidine, heat to reflux for 5 h, after the reaction is completed, cool to room temperature, evaporate acetonitrile under reduced pressure, add water and stir for 0.5 h, filter to obtain a white solid, wash with methanol, and dry After drying, about 29.9 g of 2-(4,6-dichloropyrimidin-2-yl)-1-(2-methoxycarbonylphen-1-yl)sulfonylurea was obtained, with a purity of 92% and a yield of 80.9%.

Embodiment 2

[0024] Example 2: 2-(4,6-dimethoxypyrimidin-2-yl)-1-(3-dimethylcarbamoylpyridin-2-yl)sulfonylurea

[0025] Weigh 24.8g of 3-dimethylcarbamoyl-2-sulfonyl chloride pyridine and place it in the reactor, add 100mL of toluene, 6.6g of NaOCN, and 0.92g of benzyltriethylammonium chloride into the reaction solution. After stirring at room temperature for 1 h, 155.16 g of 4,6-dimethoxy-2-aminopyrimidine was added, and the following operations were the same as in Example 1 to obtain the product 2-(4,6-dimethoxypyrimidin-2-yl)-1- (3-Dimethylcarbamoylpyridin-2-yl)sulfonylurea 39.6g, purity 94.4%, yield 91.2%.

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Abstract

The invention discloses a method for synthesizing a sulfonylureas compound under phase-transfer catalysis. The method is characterized in that pyridine (benzene) sulfonyl chloride, cyanate and aminoheterocycle compound react in a solvent at 0-150 DEG C with the presence of a the phase-transfer catalyst PTC to prepare the sulfonylureas compound; and the reaction equation is as follows. In the method, the phase-transfer catalysis is applied to the reaction of the sulfonylurea, and a pot boiling method can be adopted for the reaction so that the operation is simple and convenient; in addition, since the existence of the phase-transfer catalyst, the opportunity of the contact between insoluble cyanate negative ions and sulfonyl positive ions is increased during the reaction, the reaction yield is greatly enhanced, and the cost is reduced.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to a synthesis method of sulfonylurea compounds. Background technique [0002] Sulfonylurea ultra-efficient herbicides have become a milestone in the history of pesticide creation due to their ultra-efficiency, low toxicity, and ultra-low dosage. Its use has greatly improved the impact of the use of pesticides on the environment, and quickly set off an upsurge internationally. Many large pesticide companies in the world have invested a lot of energy and financial resources in the research of sulfonylurea herbicides, and have made remarkable achievements, such as monosulfuron-methyl, chlorimuron-methyl, nicosulfuron and many other excellent products. . A lot of researches have also been put into the synthesis of sulfonylurea compounds. The early synthesis method generally uses isocyanate and amino heterocyclic compound to condense in an organic solvent. Isocyanate reacts w...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/42C07D401/12B01J31/02B01J31/06
Inventor 徐强李维思陈新春杜翔张阿金
Owner NANJING HUAZHOU PHARMA
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