Method for preparing azoxystrobin and its analogue

A technology for pyrimidine and compound, which is applied in the field of novel preparation of agricultural fungicide azoxystrobin and its analogs, can solve problems such as deprotection and increase of raw material intermediates, and achieve the effect of simplifying production process and improving yield

Active Publication Date: 2008-04-09
SHANGYU NUTRICHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Method (B) is the first route introduced, and it is also the first synthetic method introduced in the patent literature. Although thi...

Method used

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  • Method for preparing azoxystrobin and its analogue
  • Method for preparing azoxystrobin and its analogue
  • Method for preparing azoxystrobin and its analogue

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Preparation of 2-(2-(6-(2-cyanophenoxy)pyrimidine-4-oxyl)phenyl)acetic acid methyl ester (i.e. R 1 is the general formula (II) compound of 6-(2-cyanophenoxypyrimidin)-4-yl)

[0031] Under the protection of dry nitrogen, 540ml of dry N,N-dimethylformamide, 26.2g of 2-hydroxybenzonitrile, 29.8g of 4,6-dichloropyrimidine and 27.6g of anhydrous potassium carbonate were successively added to the reaction flask . Start stirring, heat to 100°C, and stir for 3 hours. Subsequently, 34.9 g of methyl 2-hydroxyphenylacetate and 13.8 g of anhydrous potassium carbonate were added, the temperature was raised to 120° C., and the reaction was stirred for 5 hours. After concentrating under reduced pressure to recover N,N-dimethylformamide, 150ml of toluene and 100ml of water were added to the residue, stirred to dissolve the solid, left to stand, and separated into layers. The organic phase was concentrated, and the obtained solid was methyl 2-(2-(6-(2-cyanophenoxy)pyrimidine-4-oxyl)p...

Embodiment 2

[0033] Preparation of (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxymethyl acrylate (Azoxystrobin)

[0034]

[0035] Under the protection of dry nitrogen, 150ml of dichloromethane and 11.4g of titanium tetrachloride were successively added into the reaction flask, and then 6.4g of trimethyl orthoformate was added under vigorous stirring. After stirring at room temperature for 1 hour, the reaction liquid was cooled to 0°C, and 18.1 g of methyl 2-(2-(6-(2-cyanophenoxy)pyrimidine-4-oxyl)phenyl)acetate was added. After stirring for 30 minutes, 12.1 g of triethylamine was added and stirred at room temperature for 1 hour. The resulting reaction mixture was washed with 40 ml of 10% hydrochloric acid, dried over anhydrous magnesium sulfate, and stripped in vacuo to obtain a brown viscous substance. The brown sticky substance was dissolved in 100ml of hot toluene, cooled to room temperature, and 0.9g of benzyltriethylammonium chloride, 15g of 20% aqueous sodium hyd...

Embodiment 3

[0037] Preparation of (E)-2-(2-(6-chloropyrimidine-4-oxyl)phenyl)-3-methoxymethyl acrylate

[0038]

[0039]Under the protection of dry nitrogen, 150ml of dichloromethane and 11.4g of titanium tetrachloride were successively added into the reaction flask, and then 6.4g of trimethyl orthoformate was added under vigorous stirring. After stirring at room temperature for 1 hour, the reaction solution was cooled to 0° C., and 13.9 g of methyl 2-(2-(6-chloropyrimidine-4-oxy)phenyl)acetate was added. After stirring for 30 minutes, 12.1 g of triethylamine was added and stirred at room temperature for 1 hour. The resulting reaction mixture was washed with 40 ml of 10% hydrochloric acid, dried over anhydrous magnesium sulfate, and stripped in vacuo to obtain a brown viscous substance. The brown sticky substance was dissolved in 100ml of hot toluene, cooled to room temperature, and 0.9g of benzyltriethylammonium chloride, 15g of 20% aqueous sodium hydroxide solution and 12.6g of dime...

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Abstract

The invention relates to a preparation method of a compound with general formula (I), the preparation method includes: (1) the compound with general formula (II) and the formylation reagent are carried out the formylation reaction with the presence of Lewis acid and the organic base at -20 DEG C to 100 DEG C, and then the tertiary amine is added for reaction for a period of time; (2) the product of step (1) is carried out the methylation reaction with the inorganic base and the methylation reagent at -10 DEG C to 100 DEG C, so as to get the compound with general formula (I).

Description

technical field [0001] The invention relates to a novel preparation method of the agricultural fungicide azoxystrobin and its analogues. Background technique [0002] Azoxystrobin is the first β-methoxyacrylate fungicide developed and commercialized by Zeneca, and its chemical name is (E)-2-{2-[6-(2- Methyl cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate, whose mechanism of action is an inhibitor of mitochondrial respiration, that is, through the cytochrome b and C 1 Inter-electron transfer inhibits mitochondrial respiration. Due to the high efficiency and broad spectrum of the fungicide, it can prevent and control almost all diseases of fungi, oomycetes, phycomycetes, ascomycetes and deuteromycetes, and can be used in grains, rice, grapes, potatoes, It is used on vegetables, fruit trees, beans and other crops, so there are many patent documents reporting its synthesis method, such as patent EP-A-0382375, WO92 / 08703A1, GB229174 and so on. [0003] [0004] Azo...

Claims

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Application Information

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IPC IPC(8): C07D239/52
CPCC07D239/52C07D239/34C07C67/31C07C67/343C07C69/734C07C69/738
Inventor 刘尚钟母灿先王文军陈建伟王曙光
Owner SHANGYU NUTRICHEM
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