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Preparation method of Azoxystrobin and intermediate thereof

一种化合物、当量的技术，应用在嘧菌酯及其中间体的制备领域，能够解决反应总收率低、原材料成本高等问题，达到反应总收率高、降低原材料成本的效果

Active Publication Date: 2019-10-01
PAPANNA BEIJING TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The purpose of the present invention is to overcome the problems of low total reaction yield and high cost of raw materials in the preparation of azoxystrobin in the prior art, and provide a method for preparing azoxystrobin and its intermediates

Method used

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  • Preparation method of Azoxystrobin and intermediate thereof
  • Preparation method of Azoxystrobin and intermediate thereof
  • Preparation method of Azoxystrobin and intermediate thereof

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preparation example Construction

[0037] The present invention also provides a preparation method of the compound shown in formula (I), the method comprising the following steps:

[0038] (1) Under acidic conditions, the compound shown in the formula (II) prepared above is hydrolyzed in an organic solvent to prepare the compound shown in the formula (III);

[0039] (2) reacting the compound shown in the formula (III) with a base and a methylating reagent to prepare the compound shown in the formula (I);

[0040]

[0041] In the formula, R 3 for hydrogen or C 1 -C 4 Alkyl, R 4 for C 1 -C 4 alkyl.

[0042] In the present invention, the cost of raw materials for preparing azoxystrobin is low, and the total reaction yield of azoxystrobin is greatly improved by using the intermediate of azoxystrobin, that is, the compound represented by formula (II) as a raw material.

[0043] In the present invention, based on the amount of the compound represented by formula (II) as 1.00 molar equivalents, the amount of...

Embodiment 1

[0058] Preparation of 2-(2-(6-chloropyrimidine-4-oxyl group) phenyl)-3-dimethylaminoacrylate methyl ester (ie Z 1 is chlorine, R 3 , R 4 is the general formula (II) compound of methyl)

[0059] In the four-neck flask equipped with mechanical stirring, thermometer, and condenser tube, add 19.5g (0.1mol, 99%) dimethylaminomethenyl benzofuranone (that is, in formula IV, R 3 , R 4 methyl compound) and 150mL toluene, followed by adding 5.5g (0.1mol, 99%) solid sodium methoxide, stirring the reaction at room temperature for 3h, cooling to -15°C, then adding 0.1g triethylenediamine, and simultaneously adding 4, 6-dichloropyrimidine was stirred for 5 hours and then raised to room temperature, washed with water and separated, and the organic phase was concentrated to obtain a solid that was 2-(2-(6-chloropyrimidine-4-oxyl)phenyl)-3-dimethylaminoacrylic acid The methyl ester was directly carried out to the next step reaction without separation. It was measured that the yield of met...

Embodiment 2

[0061] The preparation of 2-(2-(6-(2-cyanophenoxy group) pyrimidine-4-oxyl group) phenyl)-3-dimethylaminoacrylate (i.e. in the formula (II), Z 1 is 2-cyanophenyl, R 3 , R 4 for methyl compounds)

[0062] In a four-neck flask equipped with mechanical stirring, a thermometer, and a condenser tube, add 34 g (0.1mol, 98%) of the product of Example 1 2-(2-(6-chloropyrimidine-4-oxyl)phenyl)- 3-Methylaminoacrylate, 12.0g salicylonitrile and 100mL N,N-dimethylformamide, add 15.5g (0.1mol, 98%) potassium carbonate, add 0.1g triethylenediamine, heat up to 80 ℃ and stirred for 3 hours, then distilled off the solvent N,N-dimethylformamide under reduced pressure, then added toluene to dissolve, and washed with water to separate layers, and the solid obtained by concentrating the organic phase was 2-(2-(6-(2-cyano (phenoxy)pyrimidin-4-oxy)phenyl)-3-dimethylaminoacrylate methyl ester. It was measured that the yield of methyl 2-(2-(6-(2-cyanophenoxy)pyrimidine-4-oxyl)phenyl)-3-dimethylami...

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Abstract

The invention relates to the field of preparation of Azoxystrobin, and discloses a preparation method of a compound shown in a formula (I). The method comprises the following steps of (1) under the acid condition, enabling a compound shown in a formula (II) to generate hydrolysis reaction in a solvent, so as to obtain a compound shown in a formula (III); (2) enabling the compound shown in the formula (III) to react with alkaline and a methylation reagent, so as to obtain the compound shown in the formula (I), wherein R3 is hydrogen or C1-C4 alkyl group; R4 is C1-C4 alkyl group. The preparationmethod of the Azoxystrobin has the advantages that by adopting the technology, the trimethyl orthoformate is replaced, so that the cost of the raw material is reduced, the total yield rate in reaction is high, and the preparation method is suitable for large-scale industrialized production; proofed by experiment, the yield rate of the prepared Azoxystrobin can reach 95%.

Description

technical field [0001] The invention relates to the field of preparation of the agricultural fungicide azoxystrobin, in particular to a preparation method of azoxystrobin and an intermediate thereof. Background technique [0002] Azoxystrobin (Azoxystrobin) is a methoxyacrylate fungicide developed and commercialized by Zeneca Corporation (now Syngenta). It is currently the world's largest agricultural fungicide product. Azoxystrobin is a high-efficiency, broad-spectrum, new-type fungicide, which can prevent and control almost all fungi, oomycetes, phycomycetes and other diseases. It is widely used in crops such as grains, rice, grapes, potatoes, and fruit trees. [0003] At present, the technologies used for the industrial production of azoxystrobin basically refer to the technologies disclosed in the prior art EP0592435A1 and US2008214587A1. Generally, benzofuranone reacts with trimethyl orthoformate under the condition of acetic anhydride to generate 3-methoxymethenyl-2-b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/52
CPCC07D239/52
Inventor 刘彬龙张贤军徐格王志会
Owner PAPANNA BEIJING TECH
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