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Azoxystrobin synthesis method

A synthetic method, azoxystrobin technology, applied in the field of chemical product production

Active Publication Date: 2013-06-12
HEBEI VEYONG BIO CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0016] The process takes a long time to react, requiring more than 40 hours, and the by-product chloromethoxypyrimidine is produced during the reaction
On the other hand, the intermediate (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate methyl ester has low reactivity with 2-cyanophenol and requires Only react at high temperature or in the presence of a catalyst

Method used

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Examples

Experimental program
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Effect test

example 1

[0038] Preparation of Example 1 4-chloro-6-(2-cyanophenoxy)pyrimidine:

[0039](1) 13.8g (0.10mol) of 2-chlorobenzonitrile, 10.65g (0.095mol) of 4,6-dihydroxypyrimidine, 13.8g (0.10mol) of anhydrous potassium carbonate, 0.5gCuCl (0.005mol) and 50mL Sulfolane was added into a 250ml four-neck flask reactor, and the reaction was carried out under nitrogen protection. Raise the temperature to 95°C for 1 hour, then raise the temperature to 135°C for 13 hours. Then it was slowly lowered to room temperature, separated by filtration, and the solvent was removed to obtain 19.64 g of a light yellow solid, which was 4-hydroxy-6-(2-cyanophenoxy)pyrimidine.

[0040] (ii) Add 63.4ml (0.45mol) of phosphorus oxychloride to the above 19.64g of solid 4-hydroxy-6-(2-cyanophenoxy)pyrimidine, cool down to 0°C, and dropwise add 40.4g (0.2mol) of triethylamine After dripping, keep warm for 2h, slowly raise the temperature to 80°C, keep warm and reflux for 5h. The reaction mixture was cooled and t...

example 2

[0042] Example 2 Preparation of 4-chloro-6-(2-cyanophenoxy)pyrimidine

[0043] (1) 13.8g (0.10mol) 2-chlorobenzonitrile, 12.78g (0.114mol) 4,6-dihydroxypyrimidine, 14.49g (0.105mol) anhydrous potassium carbonate, 0.5g (0.005mol) CuCl and 50mLN- Methylpyrrolidone was added into a 250ml four-necked flask reactor, and reacted under nitrogen protection. Raise the temperature to 95°C for 1 hour, then raise the temperature to 140°C for 11 hours. Then it was slowly lowered to room temperature, separated by filtration, and the solvent was removed to obtain 20.4 g of a light yellow solid, which was 4-hydroxy-6-(2-cyanophenoxy)pyrimidine.

[0044] (ii) Add 63.4ml (0.45mol) of phosphorus oxychloride to the above 20.4g of solid 4-hydroxy-6-(2-cyanophenoxy)pyrimidine, cool down to 0°C, and dropwise add 40.4g (0.2mol) of triethylamine After dripping, keep warm for 2h, slowly raise the temperature to 80°C, keep warm and reflux for 5h. The reaction mixture was cooled and the solvent was re...

example 3

[0046] Example 3 Preparation of (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxymethyl acrylate (compound I):

[0047] In a 250ml four-necked flask reactor, 21.0g (0.10mol) (E)-2-(2-hydroxyphenyl)-3-methoxymethyl acrylate and 25.48g (0.11mol) 4-chloro-6- (2-cyanophenoxy)pyrimidine was dissolved in 60mL N,N-dimethylformamide, 20.7g (0.15mol) of anhydrous potassium carbonate and 0.36g (0.003mol) of 4-dimethylaminopyridine were added, in Under the protection of nitrogen, the temperature was raised to 60° C. for 3.5 h. After cooling down to room temperature, a brown-red solid was obtained through precipitation. The solid was dissolved in 100mL of toluene, added with 50mL of water, washed and concentrated under reduced pressure (using a water bath temperature of 60°C) to obtain 38.2g of a crude product with a content of 92.0% and a yield of 87.2%.

[0048] Add 40ml of methanol to 38.2g of the above crude product, heat up to 70°C and reflux for 2h, cool down to 0-5°...

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Abstract

The invention relates to an azoxystrobin synthesis method which comprises the following synthesis steps: performing coupling reaction on 2-chlorobenzonitrile and 4,6-dihydroxypyrimidine in high-boiling-point aprotic solvent in the presence of a palladium or copper catalyst under alkaline conditions to generate 4-hydroxy-6-(2-cyanophenoxy)pyrimidine; chlorinating to obtain 4-chloro-6-(2-cyanophenoxy)pyrimidine; coupling the 4-chloro-6-(2-cyanophenoxy)pyrimidine with methyl (E)-2-(2-hydroxyphenyl)-3-methoxyacrylate in high-boiling-point aprotic solvent in the presence of a copper catalyst or a tertiary amine catalyst under alkaline conditions to generate methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidine-4-yloxy]phenyl}-3-methoxyacrylate. The invention optimizes the reaction conditions, shortens the reaction time, avoids the generation of impurities, simplifies the separation and after treatment process, and is high in product yield and good in quality. Besides, the raw materials in the invention are cheap and accessible, thereby achieving low cost and being suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical product production, and relates to a method for preparing an agricultural fungicide, in particular to a method for synthesizing azoxystrobin. Background technique [0002] Azoxystrobin is a methoxyacrylate fungicide with the chemical name (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy] Methyl phenyl}-3-methoxyacrylate. Due to the high efficiency and broad spectrum of the fungicide, it is effective against almost all fungal diseases (oomycetes, phycomycetes, ascomycetes and deuteromycetes) such as powdery mildew, rust, glume blight, net spot, downy mildew , rice blast, etc. have good activity. The dosage should be controlled at 25-200g / hm 2 , and use it on cereals, rice, grapes, potatoes, vegetables, fruit trees, beans and other crops through stem and leaf treatment and seed treatment. Azoxystrobin is the most widely used fungicide in the world, and a large number of patent documents disclose ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/52
Inventor 祁同生赵娜马彩霞次素英张丽荣赵立峰贾成国
Owner HEBEI VEYONG BIO CHEM
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