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The synthetic method of azoxystrobin

A synthesis method and technology of azoxystrobin are applied in the field of synthesis of phenoxypyrimidine derivatives, which can solve the problems of consuming catalysts and increasing the difficulty of wastewater treatment.

Active Publication Date: 2016-09-28
CHONGQING UNISPLENDOUR CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After the reaction, the catalyst enters the wastewater, which consumes more expensive catalysts and increases the difficulty of wastewater treatment.

Method used

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  • The synthetic method of azoxystrobin
  • The synthetic method of azoxystrobin
  • The synthetic method of azoxystrobin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Suspend 10g of silica gel in 250mL of toluene, stir, heat to reflux, drop 15mL of chloromethyltrimethoxysilane, reflux for 24h, cool to room temperature, filter, wash the solid with toluene and dichloromethane, and dry under reduced pressure at 70°C for 5h The resulting solid was put into a 1000mL four-neck round bottom flask, added 7.5g triethylenediamine and 600mL acetone, stirred, heated to reflux for 24h, cooled to room temperature, filtered, and the solid was washed once with acetone and dichloromethane, 50 °C and dried under reduced pressure for 5 h to obtain triethylenediamine catalyst 1 supported on silica gel.

Embodiment 2

[0084] 10g of silica gel was suspended in 250mL of toluene, stirred, heated to reflux, 18mL of 3-iodopropyltrimethoxysilane was added dropwise, refluxed for 24h, cooled to room temperature, filtered, the solid was washed with toluene and dichloromethane respectively, and reduced pressure at 70°C Dry for 5h; put the obtained solid into a 1000mL four-neck round bottom flask, add 7.5g of triethylenediamine and 600mL of acetone, stir, heat and reflux for 24h, cool to room temperature, filter, and wash the solid once with acetone and dichloromethane , dried under reduced pressure at 50° C. for 5 h to obtain triethylenediamine catalyst 2 supported on silica gel.

Embodiment 3

[0086] (1) Synthesis of methyl 2-(2-hydroxyphenyl)-3,3-dimethoxypropionate

[0087] Add 179.6g (98%, 1.0mol) of 3-(α-methoxy)-methylenebenzofuran-2(3H)-one and 400mL methanol into a 1000mL four-neck flask, stir well and cool to -5 -0°C, add 198g of sodium methoxide methanol solution (30%, 1.1mol) dropwise at this temperature, continue to keep warm for 1h after the dropwise addition, the reaction solution is neutralized with acetic acid, and then extracted with dichloromethane (3×300mL), Dry over anhydrous sodium sulfate, filter, the filtrate is distilled under reduced pressure to recover dichloroethane, and the distillation residue is methyl 2-(2-hydroxyphenyl)-3,3-dimethoxypropionate (224.4g, content 92%), yield 86%.

[0088] (2) Synthesis of methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionate

[0089] 15.2g (98%, 0.1mol) of 4,6-dichloropyrimidine, 6.0g of sodium carbonate (99%, 0.056mol), 2-(2-hydroxyphenyl)-3,3- Methyl dimethoxypropionate 26.0g (92%, 0...

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Abstract

The invention discloses a method for synthesizing azoxystrobin and a catalyst applied to azoxystrobin synthesis. According to the catalyst, triethylene diamine is fixedly connected to the surface of silica gel, thus, the synthetic reaction of azoxystrobin can be effectively catalyzed, the catalyst can be recovered and reused by a simple method, and the consumption of the catalyst is lowered, so that the catalyst is applicable to large-scale industrial production.

Description

technical field [0001] The invention relates to a synthesis method of phenoxypyrimidine derivatives, in particular to a synthesis method of azoxystrobin and a special catalyst. Background technique [0002] Azoxystrobin is a methoxyacrylate fungicide with the chemical name (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl] - Methyl 3-methoxyacrylate. The fungicide is broad-spectrum and highly effective, and has good activity against almost all fungal diseases such as powdery mildew, rust, glume blight, net spot, downy mildew, and rice blast. Azoxystrobin is the most widely used fungicide in the world. A large number of patent documents disclose its synthesis method. At present, there are three main routes for the synthesis of azoxystrobin: [0003] Route 1: Synthesis of azoxystrobin from methyl (E)-2-[2-(6-pyrimidin-4-yloxy)phenyl]-3-methoxyacrylate and salicylonitrile or its salt. [0004] [0005] A kind of synthetic method of azoxystrobin is disclosed in WO920870...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/52B01J31/02
CPCB01J31/0254B01J2231/4288C07D239/52
Inventor 丁永良吴传隆张飞游欢刘佳何咏梅
Owner CHONGQING UNISPLENDOUR CHEM