Synthetic method for azoxystrobin intermediate

A synthesis method and intermediate technology, which are applied in the synthesis field of azoxystrobin intermediates, can solve the problems of complicated operation, low yield, many by-products, etc., and achieve the advantages of lowering reaction temperature, improving yield and reducing loss of raw materials. Effect

Inactive Publication Date: 2017-11-17
SHANGHAI INST OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] For the above-mentioned technical problems in the prior art, the object of the present invention is to provide a kind of synthetic method of new azoxystrobin intermediate; The synthetic method of azoxystrobin intermediate of the present invention will solve complicated and miscellaneous operation in the prior art, by-product Many, low yield technical problems

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  • Synthetic method for azoxystrobin intermediate
  • Synthetic method for azoxystrobin intermediate
  • Synthetic method for azoxystrobin intermediate

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Add benzofuranone 400g (2.98mol) trimethyl orthoformate 600g (5.66mol) and acetic anhydride 670ml in the four-necked flask, and add a rectifying column with a length of 20cm on the bottleneck, and the filler is a glass spring. Distillation reaction is carried out, the temperature in the reaction bottle is slowly raised to 95-100°C, the temperature is raised for about 2-3h, and the temperature is kept for about 10h. During the reaction process, the low-boiling methyl acetate produced by the reaction is distilled through the rectification column to reduce the entrainment of raw materials such as trimethyl orthoformate and acetic anhydride, and it is slightly cooled and distilled under reduced pressure to 100°C. 1h, add toluene and stir to dissolve, and directly use the next step without treatment (quantitative yield 96.5%).

[0025] Add 488g of 2,6-dichloropyrimidine to a four-neck flask, add 900ml of toluene, add the condensate toluene solution from the previous step, ad...

Embodiment 2

[0027] Add benzofuranone 400g (2.98mol) trimethyl orthoformate 505g (4.76mol) and acetic anhydride 600ml in the four-necked flask, and add a rectifying column with a length of 40cm on the bottleneck, the packing is a ceramic packing, Distillation reaction is carried out, the temperature in the reaction bottle is slowly raised to 95-100°C, the temperature is raised for about 2-3h, and the temperature is kept for about 10h. During the reaction process, the low-boiling methyl acetate produced by the reaction is distilled through the rectification column to reduce the entrainment of raw materials such as trimethyl orthoformate and acetic anhydride, and it is slightly cooled and distilled under reduced pressure to 100°C. 1h, add toluene and stir to dissolve, and directly use the next step without treatment (quantitative yield 93.3%).

[0028] Add 488g of 2,6-dichloropyrimidine to the four-neck flask, add 900ml of toluene, add the condensate toluene solution from the previous step, ...

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Abstract

The invention discloses a synthetic method for an azoxystrobin intermediate. The method comprises the following steps: firstly, benzofuranone, trimethyl orthoformate and acetic anhydride are used as raw materials, reactive distillation operation is performed, and thus condensation substances are obtained by a one-pot method with a high yield; and secondly, a one-pot method reaction is performed on the condensation substances and 2,6-dichloropyrimidine in a methanol solution of sodium methylate; and finally, after the reaction is finished, the acidity is regulated, methanol is recycled, alkali washing is performed, a catalyst of p-toluenesulfonic acid is added to the condensed crude products, a reaction is performed, and thus the azoxystrobin intermediate (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate is obtained. The method is simple in operation, high in yield, less in by-products, and suitable for industrialized production.

Description

technical field [0001] The invention belongs to the technical field of chemical product production, and relates to a method for synthesizing a pesticide intermediate, in particular to a method for synthesizing an azoxystrobin intermediate. Background technique [0002] Azoxystrobin has a very broad bactericidal spectrum, and it has excellent activity against almost all fungal diseases such as powdery mildew, rust, scab, downy mildew, rice blast, etc. use, and has little impact on crop planting; efficient bactericidal effect and excellent economic benefits are the core factors for its success. Azoxystrobin has good physical and chemical properties and can be prepared into various preparations, including: wettable powder, water dispersible granule agent, suspending agent, etc. (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methyl methoxyacrylate is its most critical intermediate, and its structure is as shown in (I): [0003] [0004] There are two main synthetic routes fo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/34
CPCC07D239/34Y02P20/10Y02P20/582
Inventor 王朝阳毛海舫姚跃良陈红田谢陈世华
Owner SHANGHAI INST OF TECH
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