Method for preparing fluacrypyrim

A technology for pyrimidine and trifluoromethylpyrimidine, which is applied in the field of synthesis of the acaricide pyrimidine, can solve the problems of difficult recovery and reuse of organic solvents, large usage of organic solvents, limited capacity of chromatographic columns, etc. Low, shorten the reaction time, the effect of improving the yield

Active Publication Date: 2019-04-26
LIUZHOU HUINONG CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This side reaction means that one equivalent of methyl ester will be hydrolyzed for every equivalent of pyrimidin, resulting in the loss of methyl ester raw material, and the hydrolyzed product is difficult to remove through post-treatment operations, and the product needs to be separated by column
The technical level that can be achieved in the comparative literature can only stay within 100g, and the target product needs to be obtained through column separation. The column separation method uses a large amount of

Method used

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  • Method for preparing fluacrypyrim

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) Add 20 g (0.083 moL) of (E)-2-(2'-chloromethyl)phenyl-3-methoxymethyl acrylate, 2-iso Propoxy-4-hydroxy-6-trifluoromethylpyrimidine 22.15g (0.100moL), potassium carbonate 6.32g (0.046moL) and DMF189.6g, stirred and dissolved, heated to 120°C, TLC followed the reaction to (E) - Methyl 2-(2'-chloromethyl)phenyl-3-methoxyacrylate is completed.

[0031] (2) Pour the feed liquid into 200g of 0.5% sodium hydroxide aqueous solution after cooling, stir and separate out viscous matter, extract 80g × 3 times with industrial ethyl acetate, wash with water, dry, and concentrate under reduced pressure until dry to obtain orange-red oily 37g of the product (i.e. pyrimiden crude product) was used for refining.

[0032] (3) Add 140g of ethanol to the crude product of pyrimidone, heat to dissolve and transfer it into a 500mL three-neck flask with mechanical stirring and a thermometer, stir and heat to reflux, then suction filter while it is hot, and re-transfer the filtrate into a ...

Embodiment 2

[0034] (1) Add 90 g (0.37 moL) of (E)-2-(2'-chloromethyl)phenyl-3-methoxymethyl acrylate to a 3000 mL three-necked flask equipped with a mechanical stirrer and a thermometer, 2-iso Propoxy-4-hydroxyl-6-trifluoromethylpyrimidine 99g (0.45moL), potassium carbonate 54g (0.39moL) and DMF900g, stirred and dissolved, heated to 120 ° C, TLC followed the reaction to (E)-2-( Methyl 2'-chloromethyl)phenyl-3-methoxyacrylate is completed.

[0035] (2) Pour the feed liquid into 900g of 0.5% aqueous sodium hydroxide solution after cooling, stir and separate out viscous matter, extract 360g × 3 times with industrial ethyl acetate, wash with water, dry, and concentrate under reduced pressure to dryness to obtain orange-red oily 170g of the product (i.e. the crude product of pyrimidin) was all used for refining.

[0036] (3) Add 810g of ethanol to the crude product of pyrimidin, heat to dissolve and then transfer it into a 3000mL three-necked flask with mechanical stirring and a thermometer. ...

Embodiment 3

[0038] (1) Add 720 g (2.99 moL) of (E)-2-(2'-chloromethyl)phenyl-3-methoxymethyl acrylate to a 10L three-necked flask with mechanical stirring and a thermometer, 2- 792g (3.56moL) of isopropoxy-4-hydroxyl-6-trifluoromethylpyrimidine, 216g (1.56moL) of potassium carbonate and 7.2kg of DMF, stirred and dissolved, heated to 135°C, TLC tracked the reaction to (E)- Methyl 2-(2'-chloromethyl)phenyl-3-methoxyacrylate is completed.

[0039] (2) feed liquid is poured in the 0.5% sodium hydroxide aqueous solution of 7.2kg after cooling, stirs and separates out viscous thing, industrial ethyl acetate extracts 2.8kg * 3 times, washes with water, dries, and concentrates under reduced pressure to dryness to obtain orange 1.4kg of red oily substance (ie pyrimaben crude product) was used for refining.

[0040] (3) Add 6.5kg of ethanol to the crude pyrimidofen oil, heat to dissolve and transfer it into a 10L three-necked flask with mechanical stirring and a thermometer, stir and heat to reflu...

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Abstract

The invention discloses a method for preparing fluacrypyrim. The method comprises the following steps: firstly, etherification reaction: taking (E)-2-(2'-chloromethyl) phenyl-methyl 3-methoxyacrylateand 2-isopropoxy-4-hydroxy-6-trifluoromethyl pyrimidine as raw materials, adding the raw materials into a solvent DMF and adding K2CO3 as an acid-binding agent at the same time; carrying out a reaction at 120 to 150 DEG C, ending the reaction until the (E)-2-(2'-chloromethyl) phenyl-methyl 3-methoxyacrylate disappears to obtain feed liquid and cooling the feed liquid to room temperature; secondly,extraction of crude products: adding the cooled feed liquid into an alkali aqueous solution and stirring to obtain a viscous material; then extracting, washing, drying and concentrating to be dry toobtain a crude product of the fluacrypyrim; thirdly, refining: recrystallizing the crude product of the fluacrypyrim, thus obtaining a fluacrypyrim product with the purity of not less than 96 percent.The method disclosed by the invention has the advantages of high industrial feasibility, higher yield, more stable quality, lower cost, high safety and environment friendliness.

Description

technical field [0001] The invention belongs to the field of synthesis of the acaricide pyrimaben, in particular to a method for preparing pyrimaben. Background technique [0002] Pyrimiden is the first methoxyacrylate acaricide developed by BASF and Soda Corporation of Japan. The principle of insecticide is mainly to inhibit the mitochondrial respiration of insects and cause the death of insects. It is mainly used to control citrus. Mites of various fruits such as apples. At present, there are few types of effective acaricides in China, and the synthesis process of pyrimidaben is still in the stage of laboratory research and development in China. Synthesis and acaricidal activity of esters. "Pesticides", Volume 48, No. 3, March 2009.) It does not yet have the possibility of industrial production. [0003] The synthetic route that comparative literature adopts is as follows: [0004] [0005] The response is an SN 2 The reaction mechanism is that 2-isopropoxy-4-hydrox...

Claims

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Application Information

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IPC IPC(8): C07D239/52
CPCC07D239/52
Inventor 刘海亮曾梓韦庆书
Owner LIUZHOU HUINONG CHEM
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