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Method for synthesizing 2-cyano-3,6-dichloropyridine

A dichloropyridine and synthesis method technology, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, organic chemistry, etc., can solve the problem of increased post-processing burden, low total yield, and environmental hazards and other problems, to achieve the effect of avoiding low total yield, reducing operating risks, and reducing the hazards of waste acid

Inactive Publication Date: 2009-12-16
NANJING NO 1 PESTICIDE GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation of 2-cyano-3,6-dichloropyridine mainly contains the following two methods: US4766219, with 2,3,6-trichloropyridine as raw material, the product is obtained by fluorination and cyanation of 2-position chlorine, fluorine Cyanide generally needs highly active fluoride, such as potassium fluoride, and cyanide needs highly toxic potassium cyanide or sodium cyanide. Substances that cause great harm to the environment and increase the burden of post-processing
But still need to use highly toxic potassium cyanide or sodium cyanide as catalyst

Method used

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  • Method for synthesizing 2-cyano-3,6-dichloropyridine

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Experimental program
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Embodiment 1

[0024] 2,3,6-trichloropyridine (9.1g, 50mmol), anhydrous potassium ferrocyanide (18.4g, 50mmol), silver iodide (1.7g, 5mmol), polyethylene glycol 200 (1.0g, 5mmol), Potassium iodide (0.8 g, 5 mmol) was dissolved in N,N-dimethylformamide (250 mL), and reacted under reflux at 200° C. for 12 hours with stirring. Ethyl acetate (50-80 mL) was added, the insoluble matter was removed by filtration, and the filtrate was washed twice with 20 mL of water. The organic phase was dried over anhydrous magnesium sulfate. The solvent was rotary evaporated to obtain 6.8 g of the product 2-cyano-3,6-dichloropyridine.

Embodiment 2

[0026] 2,3,6-trichloropyridine (9.1g, 50mmol), potassium ferrocyanide trihydrate (4.22g, 10mmol), silver iodide (0.2g, 1.5mmol), polyethylene glycol 400 (0.8g, 2mmol) , Potassium iodide (0.27g, 1.5mmol) was dissolved in toluene (150mL), and reacted under reflux at 120°C for 6 hours. Ethyl acetate (60-90 mL) was added. The insoluble matter was removed by filtration, and the filtrate was washed twice with 20 mL of water. The organic phase was dried over anhydrous magnesium sulfate. The solvent was rotary evaporated to obtain 6.1 g of the product 2-cyano-3,6-dichloropyridine.

Embodiment 3

[0028] 2,3,6-trichloropyridine (9.1g, 50mmol), anhydrous potassium ferrocyanide (1.84g, 5mmol), silver iodide (1.03g, 3mmol), polyethylene glycol 1000 (2.0g, 2mmol), Potassium iodide (0.27g, 1.5mmol) was dissolved in benzene (200mL), and reacted under reflux at 40°C for 2 hours with stirring. Ethyl acetate (70-100 mL) was added. The insoluble matter was removed by filtration, and the filtrate was washed twice with 20 mL of water. The organic phase was dried over anhydrous magnesium sulfate. The solvent was rotary evaporated to obtain 4.3 g of the product 2-cyano-3,6-dichloropyridine.

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Abstract

The invention discloses a method for synthesizing 2-cyano-3,6-dichloropyridine. The method comprises the following steps of: taking 2,3,6-trichloropyridine and potassium ferrocyanide as raw materials and silver iodide-polyethylene glycol-potassium iodide as a catalyst, and putting the raw materials and the catalyst in an organic solvent for reaction for 2 to 12 hours at a temperature of between 40 and 200 DEG C to synthesize the 2-cyano-3,6-dichloropyridine, wherein the reaction molar ratio of 2,3,6-trichloropyridine, potassium ferrocyanide, silver iodide, polyethylene glycol and potassium iodide is 1:0.1-1:0.01-0.1:0.01-0.1:0.01-0.1. In the method, the 2-cyano-3,6-dichloropyridine is prepared by selecting a safe and cheap cyano group source and under reaction conditions of mildness, greenness and high efficiency, so that the method has big actual application values.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry and relates to a synthesis method of 2-cyano-3,6-dichloropyridine. Background technique [0002] As an intermediate, 2-cyano-3,6-dichloropyridine can be used to prepare other intermediates or directly prepare pesticides, especially insecticides. The preparation of 2-cyano-3,6-dichloropyridine mainly contains the following two methods: US4766219, with 2,3,6-trichloropyridine as raw material, the product is obtained by fluorination and cyanation of 2-position chlorine, fluorine Cyanide generally needs highly active fluoride, such as potassium fluoride, and cyanide needs highly toxic potassium cyanide or sodium cyanide. The substances in it cause great harm to the environment and increase the burden of post-processing. Although the product can also be directly obtained from 2,3,6-trichloropyridine by one-step cyanation, the yield is very low. Journal of Labeled Compounds and Radiopharmac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/84B01J31/26B01J31/06
Inventor 杨寿海李维思薛谊江涛蒋剑华
Owner NANJING NO 1 PESTICIDE GRP
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