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Industrial new process for synthesis of tebufenpyrad

A technology of fenpyroxim and a new process, which is applied in the field of new industrialized technology for synthesizing fenfenib, and can solve the problems of many three wastes, many reaction steps and high cost

Inactive Publication Date: 2014-12-24
天津联合益农科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Aiming at the deficiencies in the prior art of many reaction steps, high cost, and many wastes, the purpose of the present invention is to disclose a new industrial process for synthesizing tebufenpyrad, which is characterized in that: said tebufenpyrad is composed of 1-methyl- Synthesis of 3-ethyl-4-chloro-5-pyrazole carboxamide and p-tert-butylbenzyl chloride by direct nucleophilic substitution reaction

Method used

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  • Industrial new process for synthesis of tebufenpyrad

Examples

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Embodiment 1

[0011] Add 1-methyl-3-ethyl-4-chloro-5-pyrazole carboxylic acid, toluene, and thionyl chloride into the three-necked flask, and reflux for about 6 hours. The temperature of the reaction solution drops to 20°C, and concentrated ammonia water is added dropwise. After the dropwise addition, react at room temperature for 2 h, stand to separate layers, wash the organic phase with acid, dilute alkali, and saturated brine respectively, spin the solvent to dry, and recrystallize to obtain an off-white solid.

[0012] Add 1-methyl-3-ethyl-4-chloro-5-pyrazole carboxamide, p-tert-butylbenzyl chloride, triethylamine, and DMSO into the three-necked flask, heat to 120-130°C, react for 8 hours, and distill Remove the solvent, add water and stir for 30min, the aqueous phase is extracted with ethyl acetate, and the organic phase is extracted with 10% NaHCO 3 , water, and brine, and spin-dried to obtain a crude product. The obtained solid was separated by recrystallization to obtain the target ...

Embodiment 2

[0014] Add 1-methyl-3-ethyl-4-chloro-5-pyrazole carboxylic acid, toluene, and thionyl chloride into the three-necked flask, and reflux for about 6 hours. The temperature of the reaction solution drops to 20°C, and concentrated ammonia water is added dropwise. After the dropwise addition, react at room temperature for 2 h, stand to separate layers, wash the organic phase with acid, dilute alkali, and saturated brine respectively, spin the solvent to dry, and recrystallize to obtain an off-white solid.

[0015] Add 1-methyl-3-ethyl-4-chloro-5-pyrazole carboxamide, p-tert-butylbenzyl chloride, triethylamine, DMF into the three-necked flask, heat to 110-120°C, react for 8 hours, and distill Remove the solvent, add water and stir for 30min, the aqueous phase is extracted with ethyl acetate, and the organic phase is extracted with 10% NaHCO 3 , water, and brine, and spin-dried to obtain a crude product. The obtained solid was separated by recrystallization to obtain the target produ...

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Abstract

The invention discloses an industrial new process for synthesis of tebufenpyrad. The tebufenpyrad is synthesized by subjecting 1-methyl-3-ethyl-4-chloro-5-pyrazole carboxamide and p-tert-butyl benzyl chloride directly to nucleophilic substitution reaction. And the process is suitable for industrial promotion.

Description

technical field [0001] The invention relates to a new industrial process for synthesizing tebufenfen, which belongs to a synthetic process for acaricides. Background technique [0002] Tebufenpyrad is an acaricide with a pyrazole carboxamide structure discovered by Mitsubishi Corporation of Japan. It was registered in Japan in 1993. It was jointly developed by Mitsubishi, the American cyanamide company and Sandoz Corporation. It was marketed under the trade name Masai or pyranica and sold in many countries. Because of its broad-spectrum, safe and efficient acaricidal properties, it has attracted the attention of pesticide experts from all over the world. It has been reported in the literature that its synthesis methods mostly use the condensation of diethyl oxalate and butanone, hydrazine hydrate ring closure, and dimethyl sulfate methyl Chlorination, chlorination, hydrolysis, acid chlorination, and condensation with p-tert-butylbenzylamine, the reaction is a total of seven...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/16
CPCC07D231/16
Inventor 李巍尤旭东吴静
Owner 天津联合益农科技有限公司
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