Preparation method of metconazole and intermediate thereof

A technology for metconazole and intermediates, which is applied in the field of preparation of metconazole and intermediates thereof, can solve the problems of low yield, many impurities, high price and the like, and achieves the effects of easy availability of raw materials, simple process and less three wastes

Active Publication Date: 2014-03-26
JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] 1. This method requires two methylation reactions respectively, and the highly toxic compound methyl bromide is used, which is expensive and highly toxic, which is not conducive to industrial production
[0008] 2. The step of hydrolysis and decarboxylation is difficult to carry out, and the adjacent carboxyl groups with large hindr

Method used

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  • Preparation method of metconazole and intermediate thereof
  • Preparation method of metconazole and intermediate thereof
  • Preparation method of metconazole and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The present embodiment provides a kind of preparation method of metconazole, concrete implementation is as follows:

[0038] (a) Preparation of formula (2) compound 5-(4-chlorostyryl)-2-methoxycarbonylcyclopentanone

[0039] Add 142.0g p-chlorobenzaldehyde (99.0%) and 145.0g formula (1) compound 2-methoxycarbonylcyclopentanone into a 1L four-necked flask, then add 500ml methanol, heat up to reflux for 30min until completely dissolved, cool After reaching room temperature, 17.4 g of methanol solution of 28% sodium methoxide was added dropwise within 20 minutes. During the reaction, heat was released, cooled with appropriate ice water, and a light yellow solid precipitated after the drop was completed. Stir at 35°C for 4 hours, and then Cool to 5 DEG C and filter with suction, rinse the solid obtained by suction with 50ml of cold methanol, and dry to obtain a light yellow solid 5-(4-chlorostyryl)-2-methoxycarbonylcyclopentanone (that is, formula (2 ) compound) 258.0g, it...

Embodiment 2

[0053] The present embodiment provides a kind of preparation method of metconazole, concrete implementation is as follows:

[0054] (a) Preparation of formula (2) compound 5-(4-chlorostyryl)-2-methoxycarbonylcyclopentanone

[0055] Add 284.0g p-chlorobenzaldehyde (99.0%) and 290.0g formula (1) compound 2-methoxycarbonylcyclopentanone into a 2L four-neck flask, then add 1000ml methanol, heat and reflux for 30min until completely dissolved, and cool to At room temperature, dropwise add 37.0 g of methanol solution of 28% sodium methoxide within 20 minutes. Heat is released during the reaction. Cool with appropriate ice water. After dropping, a light yellow solid precipitates. Keep stirring at 35°C for 4 hours, then cool Suction filtration at 5°C, rinse the solid obtained by suction filtration with 50ml of cold methanol, and dry to obtain a light yellow solid 5-(4-chlorostyryl)-2-methoxycarbonylcyclopentanone (formula (2) Compound) 514.9g, its purity is 97.6%, the yield is 95.0% ...

Embodiment 3

[0069] The present embodiment provides a kind of preparation method of metconazole, concrete implementation is as follows:

[0070] (a) Preparation of formula (2) compound 5-(4-chlorostyryl)-2-methoxycarbonylcyclopentanone

[0071] Add 71.0g p-chlorobenzaldehyde (99.0%) and 72.5g formula (1) compound 2-methoxycarbonylcyclopentanone into a 500ml four-neck flask, then add 250ml methanol, heat and reflux for 30min until completely dissolved, and cool to At room temperature, 8.68g of methanol solution with a concentration of 28% sodium methoxide was added dropwise within 20 minutes. During the reaction, heat was released, cooled with appropriate ice water, a light yellow solid precipitated after dropping, kept stirring at 30°C for 4 hours, and then cooled Suction filtration at 5°C, the solid obtained by suction filtration was rinsed with 30ml of cold methanol, and dried to obtain a light yellow solid 5-(4-chlorostyryl)-2-methoxycarbonylcyclopentanone (that is, the formula (2) Com...

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Abstract

The invention relates to a novel method for preparing metconazole. The method takes p-chlorobenzaldehyde and 2-methoxycarbonyl cyclopentanone represented by the formula (1) as the primary raw materials, then after a series of reactions, obtains an intermediate of metconazole, namely 5-(4-chlorobenzyl)-2,2-dimethyl cyclopentanone represented by the formula (5); then subjects the intermediate to reacts with trimethylsulfonium bromide so as to obtain a reaction product, and finally subjects the reaction product to react with 1,2,4-1H-triazole so as to obtain the metconazole. The preparation method has the advantages of simple technology, available raw materials, low cost, little discharge of waste water, waste gas, and waste solid, and high content and yield of target product metconazole, wherein the metconazole content can reach 95% or more, and the total yield can reach 65% or more, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of metconazole and its intermediate. Background technique [0002] Meconazole is a triazole fungicide developed by Japan Kureha Chemical Industry Co., Ltd. and jointly developed with American Cyanamid (now BASF). [0003] Meconazole is a new broad-spectrum systemic fungicide, which has good protective and therapeutic effects, low toxicity, high fungicidal activity, less dosage, and less environmental pollution. It is mainly used for the control of dwarf rust, Leaf rust, yellow rust, crown rust, powdery mildew, glume blight, and diseases caused by Septoria and Fusarium paniculata. At present, the market share of metconazole in the domestic market is very small, and there is a lot of room for growth. [0004] The patent US7166750B1 of Japan Kureha Chemical Industry Co., Ltd. in the United States and the Chinese patent CN1454200A disclose a preparation method of 5-(4-chlorobenzyl)-2,2-dimethylcyclopentanone,...

Claims

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Application Information

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IPC IPC(8): C07C49/697C07C45/62C07D249/08
CPCC07C45/62C07C45/676C07C45/68C07C67/343C07C2601/08C07D249/08C07C49/697C07C69/757
Inventor 顾松山余强韩士芳闫立单陶亚春吕宜飞苏镜
Owner JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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