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Preparation method of cyproconazole

A technology of cyproconazole and sodium methoxide, applied in the field of preparation of cyproconazole, can solve the problems of complicated process, polluted environment, unsuitable for industrial production and the like, and achieves the effects of simple raw materials and low price

Active Publication Date: 2017-04-26
JIANGXI HUASHI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] The purpose of the present invention is to solve the problems faced by the current production of cyproconazole. The current production of cyproconazole uses a large amount of highly toxic reagents, pollutes the environment, and obtains pure products through repeated recrystallization or silica gel column chromatography. The process is relatively cumbersome. Not suitable for industrial production, and the yield is low and the purity is not high

Method used

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  • Preparation method of cyproconazole
  • Preparation method of cyproconazole
  • Preparation method of cyproconazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Add 100mL tetrahydrofuran and 15g magnesium chips (617mmol) into a 500ml three-necked flask equipped with a thermometer, a condenser, and a stirring device, and add 55.5g (411mmol) of bromomethylpropane and 37.7g of compound 1 (274mmol) dropwise under reflux. , 100mL tetrahydrofuran solution, add dropwise within about 1.5h, and then reflux for 2h, pour the reaction solution into ice water, acidify with 1N sulfuric acid, extract with methyl tert-butyl ether, combine the organic phases, wash with saturated brine, and dry. Methyl tert-butyl ether was distilled off under reduced pressure to obtain 52.3g of compound 2 with a yield of 98% and a purity of 98% (calculated as compound 1 p-chlorobenzonitrile). The nuclear magnetic spectrum of compound 2 is shown in Figure seven .

[0039] Add sodium methoxide (19.4g 360mmol) and 100mL DMF to a 500ml three-necked flask equipped with a thermometer, a condenser, and a stirring device. Compound 2 (38.9g 200mmol) is dissolved in 190m...

Embodiment 2

[0043] Add 60mL of n-hexane and 4.8g of magnesium chips (197mmol) into a 250ml three-necked flask equipped with a thermometer, a condenser, and a stirring device, and add 17.7g (131mmol) of bromomethylpropane, 18g of compound 1 (131mmol) dropwise under heating and reflux. ), 50mL of n-hexane solution, added dropwise within about 40min, and then refluxed for 2h, poured the reaction solution into ice water, acidified with 1N sulfuric acid, extracted with isopropyl ether, combined the organic phases, washed with saturated brine, dried, and reduced pressure The isopropyl ether was distilled off to obtain 20.4g of compound 2, with a yield of 80% (calculated as compound 1 p-chlorobenzonitrile)

[0044] Sodium methoxide (8.3g 154mmol) and 80mL N,N-dimethylacetamide were added to a 500ml three-neck flask equipped with a thermometer, condenser, and stirring device, and compound 2 (30.0g 154mmol) was dissolved in 150mL N,N-dimethylacetamide Methyl acetamide, then slowly added dropwise t...

Embodiment 3

[0048] Add 65mL of ether and 5.6g of magnesium chips (232mmol) into a 250ml three-necked flask equipped with a thermometer, a condenser, and a stirring device, and add 25.5g (189mmol) of bromomethylpropane and 20g of compound 1 (145mmol) dropwise under reflux. , 50 mL of diethyl ether solution, added dropwise within about 45 min, and then refluxed for 2 h, poured the reaction solution into ice water, acidified with 1N sulfuric acid, extracted with diethyl ether, combined the organic phases, washed with saturated brine, dried, and distilled off the diethyl ether under reduced pressure. Obtained 27.1g of compound 2 with a yield of 96% (calculated as compound 1 p-chlorobenzonitrile)

[0049] Sodium methylate (15.6g 288mmol) and 90mL dimethyl sulfoxide were added into a 500ml three-neck flask equipped with a thermometer, a condenser tube and a stirring device, and compound 2 (35.0g 180mmol) was dissolved in 150mL dimethyl sulfoxide, and then slowly Slowly added dropwise to sodium ...

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Abstract

The invention discloses a preparation method of cyproconazole, and belongs to the field of organic synthesis. The method particularly comprises four reactions including a Grignard-nucleophilic reaction, a nucleophilic reaction, a ring-closing reaction and a ring-opening reaction. According to the method, cyproconazole is prepared without using poisonous reagents, the process is simple, the purity and the yield are high, and the method is suitable for industrialized production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of cyproconazole. Background technique [0002] Cycloconazole as shown in formula 5 is a triazole fungicide developed by Sandoz in Switzerland, is an ergosterol demethylation inhibitor, has preventive and therapeutic effects, and is effective for cereal crops, coffee, sugar beet, The bacteria of the genera of powdery mildew, rust fungus, sporomycetes, coronospora, Septoria, and black star fungus of fruit trees and glucose are all effective, and can prevent and control cereal and coffee rust, cereal, fruit tree and grape powdery mildew, peanut, Beet leaf spot, apple scab and peanut white rot can also be mixed with other fungicides. The effective period of preventing and controlling wheat rust is 4-6 weeks, and preventing and controlling powdery mildew is 3-4 weeks. Cycloconazole was launched in France in 1989 as a fungicide for wheat foliar spray...

Claims

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Application Information

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IPC IPC(8): C07D249/08
Inventor 李文森
Owner JIANGXI HUASHI PHARMA
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