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Method for synthesizing azoxystrobin intermediate

A synthesis method and intermediate technology, applied in the field of synthesis of azoxystrobin intermediates, can solve the problems of difficult reaction, high reaction temperature, and many side reactions, and achieve mild reaction conditions, high reaction yield, and simple synthesis Effect

Inactive Publication Date: 2012-04-04
NUTRICHEM LAB CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0007] But above-mentioned synthesis method exists the problem that reaction temperature is high, side reaction is many and yield is low
And, generally use salt of wormwood as acid acceptor in the prior art, when adopting sodium carbonate, reaction is difficult to carry out

Method used

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  • Method for synthesizing azoxystrobin intermediate
  • Method for synthesizing azoxystrobin intermediate
  • Method for synthesizing azoxystrobin intermediate

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preparation example Construction

[0021] The present invention provides a method for synthesizing an azoxystrobin intermediate, the azoxystrobin intermediate having a structure represented by formula (3), wherein the method includes the following steps:

[0022] 1) Under basic conditions, the 4,6-dihalopyrimidine and the compound represented by formula (1) are subjected to the first contact reaction to obtain a product containing the compound represented by formula (2);

[0023] 2) Under alkaline conditions, in the presence of a catalyst, the compound of formula (2) is subjected to a second contact reaction with 2-hydroxybenzonitrile to obtain azoxystrobin containing the structure of formula (3). Body product

[0024]

[0025] In formulas (1), (2) and (3), R 1 Is methyl, ethyl or propyl; R 2 Is hydrogen, potassium or sodium; X is halogen; the catalyst is 1,4-diazabicyclo[2,2,2]octane and / or 2-methyl-1,4-diazabicyclo [2,2,2]octane.

[0026] The present invention provides a method for synthesizing an azoxystrobin inter...

Embodiment 1

[0055] Under the protection of nitrogen, 200ml of dry N,N-dimethylformamide (water content less than 0.5% by weight, the same below), methyl 2-hydroxyphenylacetate (33.2g, 0.2mol), 4,6-Dichloropyrimidine (29.8g, 0.2mol) and anhydrous potassium carbonate (27.6g, 0.20mol). Turn on the stirring, heat to 50°C, stir and react for 2 hours. Subsequently, 2-hydroxybenzonitrile (23.8g, 0.2mol), anhydrous potassium carbonate (22.1g, 0.16mol) and DABCO (0.114g, 0.001mol) were added, the temperature was raised to 80°C, and the reaction was stirred for 3 hours. Then, after concentration under reduced pressure to recover N,N-dimethylformamide, 150ml of dichloromethane and 100ml of water were added to the residue, stirred to dissolve the solid, after standing to separate the layers, the organic phase was separated and concentrated to obtain a solid , Add 150ml methanol to the solid and recrystallize to obtain 68.7g of yellow solid, namely methyl 2-(2-(6-(2-cyanophenoxy)pyrimidine-4-oxy)pheny...

Embodiment 2

[0061] It was carried out according to the method of Example 1, except that the amount of DABCO used was 0.045g (0.0004mol). 67.8 g of methyl 2-(2-(6-(2-cyanophenoxy)pyrimidine-4-oxy)phenyl)acetate was obtained as a yellow solid, and its melting point was determined to be 95-96°C; 1 H NMR(500MHz, CDCl 3 ): δ 3.61 (s, 3H), 3.62 (s, 2H), 6.54 (d, 1H), 7.16 (q, 1H), 7.28 (m, 1H), 7.33 (m, 1H), 7.32-7.41 ( m, 3H), 7.67 (m, 1H), 7.23 (q, 1H), 8.39 (d, 1H). In addition, the total yield of the reaction and the purity of the yellow solid are shown in Table 1.

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Abstract

The invention discloses a method for synthesizing an azoxystrobin intermediate. The synthesizing azoxystrobin intermediate has the structure shown as a formula (3). The method comprises the following steps of: under the alkaline condition, performing first contact reaction on 4,6-dihalogenopyrimidine and a compound shown as a formula (I) to obtain a product containing a compound with a structure shown as a formula (2); and under the alkaline condition, performing second contact reaction on the compound with the structure shown as the formula (2) or the product containing the compound with the structure shown as the formula (2) and 2-hydroxybenzonitrile in the presence of a catalyst to obtain the product containing the azoxystrobin intermediate with the structure shown as the formula (3), wherein the catalyst is 1,4-diazabicyclo[2.2.2]octane and / or 2-methyl-1,4-diazabicyclo[2.2.2]octane. The method for synthesizing the azoxystrobin intermediate has mild reaction conditions, is simple, has less Vilsmeier rearrangement reaction and ensures high reaction yield.

Description

Technical field [0001] The invention relates to a method for synthesizing an intermediate of azoxystrobin. Background technique [0002] Azoxystrobin is the first commercially available methoxy acrylate bactericide discovered and commercialized by Zelix, and its chemical name is (E)-2-{2-[6-(2-cyanophenoxy)pyrimidine -4-yloxy]phenyl}-3-methoxyacrylate methyl, its structural formula is as follows: [0003] [0004] Due to the high efficiency and broad spectrum of the compound, it can control almost all fungi, oomycetes, algae, ascomycetes and deuteromycetes, and can be used in grains, rice, grapes, potatoes, vegetables through stem and leaf treatment and seed treatment. , Fruit trees, beans and other crops are widely used. [0005] In the prior art, as a synthesis method of azoxystrobin, for example, CN100564362C discloses the use of Lewis acid as a catalyst, the use of a formate reagent to formylate the active methylene group of the azoxystrobin skeleton, and then methylation to pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/52
Inventor 陈建伟邓旭芳赵永长池剑鸿宋蕾王文军
Owner NUTRICHEM LAB CO LTD
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