A kind of preparation method of azoxystrobin intermediate

An intermediate, azoxystrobin technology, applied in the field of preparation of pesticide intermediates, can solve the problems of long reaction time, high production cost, and difficult purification of impurities, and achieve the effects of easy purification, improved purity, and reduced production cost

Active Publication Date: 2017-11-21
SHANGHAI TAIHE INT TRADE CO LTD +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Azoxystrobin intermediate B is a very critical intermediate for the synthesis of azoxystrobin. At present, most domestic companies are using the method described in Syngenta's patent CN1062139A, that is, compound A and dichloropyrimidine in an organic solvent at low temperature The main problems of this method are: 1) The reaction time is long, and it needs to react for 22 hours, which causes the step The energy consumption of reaction production is bigger; 2) this method yield is lower, and yield can only reach about 60~70%; 3) the impurity that produces is difficult to purify, affects product purity; 4) because the yield of this method is lower resulting in higher production costs

Method used

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  • A kind of preparation method of azoxystrobin intermediate
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  • A kind of preparation method of azoxystrobin intermediate

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Experimental program
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Effect test

Embodiment 1

[0019] 46.6 grams of compound A (98%, 0.26mol), 46.6 grams of dichloropyrimidine (98.5%, 0.308mol) and 130 milliliters of tetrahydrofuran were successively dropped into a 500 milliliter three-necked flask, stirred evenly at room temperature, and then dropped into 2-methyldivinylpiperene 0.4 g of oxazine, stirred and cooled to 15° C., began to dropwise add 53.8 grams of methanol solution of sodium methoxide (28.87%, 0.287 mol), the dropwise addition time was controlled for 5 hours, and the dropwise addition was completed and kept at 20° C. for 1 hour. Add 36% hydrochloric acid to acidify to PH = 4, add water, stir and wash twice, and desolventize to obtain the crude compound B with a yield of 80%.

Embodiment 2

[0021] 46.6 grams of compound A (98%, 0.26mol) and 130 milliliters of acetonitrile were successively dropped into a 500 milliliter three-necked flask, stirred evenly at room temperature, and then 0.4 grams of 2-methyldivinylpiperazine was dropped into, stirred and cooled to 15° C., and 53.8 Methanol solution of gram sodium methylate (28.87%, 0.287mol), dropwise time control half an hour, 20 ℃ of insulations 1 hour after dropwise finishing, add 46.6 gram dichloropyrimidines (98.5%, 0.308mol) then. After heat preservation for 1 hour, 36% hydrochloric acid was added to acidify to PH=4, and water was added to stir and wash twice, and the compound B was precipitated to obtain crude compound B with a yield of 85%.

Embodiment 3

[0023] 46.6 grams of compound A (98%, 0.26mol), 46.6 grams of dichloropyrimidine (98.5%, 0.308mol) and 130 milliliters of toluene were successively dropped into a 500 milliliter three-necked flask, stirred evenly at room temperature, and then dropped into 2-methyl divinylpiperidine 0.4 g of oxazine, stirred and cooled to 15° C., began to dropwise add 53.8 grams of methanol solution of sodium methoxide (28.87%, 0.287 mol), the dropwise addition time was controlled for 5 hours, and the dropwise addition was completed and kept at 20° C. for 1 hour. Add 36% hydrochloric acid to acidify to PH = 4, add water, stir and wash twice, and desolventize to obtain the crude compound B with a yield of 90%.

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Abstract

The present invention relates to a kind of preparation method of azoxystrobin intermediate, adopts the mode that adds catalyst to ring-opening, etherification reaction to efficiently synthesize azoxystrobin intermediate, specifically comprises the following steps: by methoxymethylene benzo Furanone and dichloropyrimidine were added into sodium methoxide / methanol solution in the presence of catalyst for ring opening and etherification reaction to synthesize azoxystrobin intermediate compound B. Compared with the prior art, the invention has the advantages of high efficiency, high yield and the like.

Description

technical field [0001] The invention relates to the preparation of a pesticide intermediate, in particular to a novel and efficient method for preparing the azoxystrobin intermediate. Background technique [0002] Azoxystrobin is currently the world's largest agricultural fungicide product, with broad-spectrum, high-efficiency, and is widely produced and used. The key intermediate compound B of azoxystrobin is generally synthesized by ring-opening and etherification reaction of methoxymethylene benzofuranone (compound A) with 4,6-dichloropyrimidine in sodium methoxide / methanol solution. Now most domestic enterprises adopt the method described in patent CN1062139A, that is, compound B is synthesized from compound A to compound B, and sodium methoxide is directly added to the ring-opening and etherification reaction without adding any catalyst. However, the yield can only be maintained at 60-60%. About 70%, the reaction produces a large amount of by-products, which directly a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/34B01J31/02
Inventor 张照军周庆江李建高田晓宏谢思勉
Owner SHANGHAI TAIHE INT TRADE CO LTD
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