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Preparation method of hexaflumuron

A technology of hexaflumuron and phenylurea, which is applied in the field of compound preparation, can solve the problems of easy self-polymerization of intermediates, difficult purification of products, and many by-products, and achieve less three wastes, great implementation value and social and economic benefits, and by-products little effect

Inactive Publication Date: 2014-12-31
QUZHOU UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a simple and reasonable process, high safety, less side reactions, easy purification of products, reaction Preparation method of hexaflumuron with high yield and product purity

Method used

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  • Preparation method of hexaflumuron

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Embodiment 1

[0028] A preparation method of hexaflumuron, said preparation method comprising the following steps:

[0029] Step (1): Dissolve 7.8g (0.12mol) of sodium cyanate in 148.2ml of water to form a 5% aqueous solution of sodium cyanate, and dissolve 7.14g (0.12mol) of acetic acid in 28.56ml of water to form a 20% aqueous solution of acetic acid , in a 500ml three-necked flask equipped with mechanical stirring, a constant pressure dropping funnel and a thermometer, sequentially add the above-mentioned aqueous acetic acid solution, 0.278g benzyltriethylammonium chloride, and then add 27.803g (0.1mol) 3, 5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)aniline, slowly add the above-mentioned aqueous solution of sodium cyanate dropwise under stirring, and an off-white solid precipitates out. After the dropwise addition, Continue to react at 0°C for 12 hours, stop the reaction, slowly pour the reaction solution into a beaker containing 176.7ml of water to dilute under stirring conditions, cool to...

Embodiment 2

[0032]Step (1): Dissolve 15.6g (0.24mol) sodium cyanate in 88.4ml water to form a 15% sodium cyanate aqueous solution, and dissolve 30g (0.5mol) acetic acid in 45ml water to form a 40% acetic acid aqueous solution. In a 500ml three-necked flask equipped with mechanical stirring, a constant pressure dropping funnel and a thermometer, add the above-mentioned aqueous acetic acid solution, 2.78g of tetrabutylammonium bromide, and 55.606g (0.2mol) of 3,5-dichloro- 4-(1,1,2,2-Tetrafluoroethoxy)aniline, under stirring, slowly add the above-mentioned aqueous solution of sodium cyanate dropwise, that is, a off-white solid precipitates, and continue to react at 80°C after the dropwise addition is completed 1h, stop the reaction, slowly pour the reaction solution into a beaker with 400ml of water under stirring conditions, dilute and cool to 5°C, filter, wash the filter cake with water until neutral, and dry to obtain an off-white solid 3,5-dichloro- 4-(1,1,2,2-tetrafluoroethoxy)phenylur...

Embodiment 3

[0035] Step (1): Dissolve 19.5g (0.3mol) of sodium cyanate in 45.5ml of water to form a 30% aqueous solution of sodium cyanate, dissolve 30g (0.5mol) of acetic acid in 20ml of water to form a 60% aqueous solution of acetic acid. In a 500ml three-necked flask equipped with mechanical stirring, a constant pressure dropping funnel and a thermometer, add the above-mentioned aqueous acetic acid solution, 1.39g of tetrabutylammonium chloride, and 55.61g (0.2mol) of 3,5-dichloro- For 4-(1,1,2,2-tetrafluoroethoxy)aniline, slowly add the above-mentioned aqueous solution of sodium cyanate dropwise under stirring, and an off-white solid precipitates out. After the addition, continue to react at 40°C for 6 hours. Stop the reaction, slowly pour the reaction solution into a beaker containing 150ml of water for dilution under stirring, cool to 2.5°C, filter, wash the filter cake with water until neutral, and dry to obtain off-white solid 3,5-dichloro-4-( 1,1,2,2-tetrafluoroethoxy)phenylurea ...

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Abstract

The invention relates to a preparation method of hexaflumuron. The preparation method of hexaflumuron taking 3, 5-dichloro-4-(1,1,2,2-tetrafluoroethoxy) aniline and sodium cyanate as raw materials comprises the following steps of: (1) adding a phase transfer catalyst in an acetic acid aqueous solution, reacting for 1-12 hours at 0-80 DEG C, filtering reaction liquid to obtain filter cakes, washing and drying to obtain 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy) phenylurea; and (2) in an organic solvent, reacting the mixture of anhydrous zinc chloride and anhydrous trichloride taken as a catalyst and 3, 5-dichloro-4-(1,1,2,2-tetrafluoroethoxy) phenylurea and 2,6-difluorobenzoyl chloride taken as raw materials for 1-24 hours at 65-150 DEG C, vacuumizing in the reaction process to remove hydrogen chloride gas, after reaction is ended, recovering the solvent through reduced pressure distillation, after cooling, adding a sodium bicarbonate solution with the mass fraction of 5%, adjusting the pH to 7-8, stirring for 30 minutes, filtering reaction liquid to obtain filter cakes, washing, drying and recrystallizing to obtain hexaflumuron. The preparation method of hexaflumuron has the advantages of being simple and reasonable in process, little in side reaction and having high safety, high reaction yield and high product purity, great industrialization potential and great social economic benefits, and can easily realize purification of products.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a preparation method of hexaflumuron, a substituted benzoylurea insect growth regulator. Background technique [0002] Hexaflumuron belongs to benzoylurea insecticide, is a chitin synthesis inhibitor, has high insecticidal and ovicidal activity, and is quick-acting, especially for the control of cotton bollworm. Used for cotton, potato and fruit trees to control various Coleoptera, Diptera and Homoptera insects. [0003] At present, there are two main synthetic methods of hexaflumuron: (1) first generate 2,6-difluorobenzoyl isocyanate from 2,6-difluorobenzamide and phosgene or oxalyl chloride, and then combine with 3,5 -Dichloro-4-(1,1,2,2-tetrafluoroethoxy) aniline reaction prepared; (2) first by 3,5-dichloro-4-(1,1,2,2-tetra Fluoroethoxy)aniline and phosgene or oxalyl chloride generate 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl isocyanate, and then react with 2,6-di...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C275/54C07C273/18
Inventor 冯晓亮谢建伟蒋国飞徐天有赵颖俊高鸿杰
Owner QUZHOU UNIV