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Method for preparing 1-tert butyl-3-(2,6-diisopropyl-4-phenyl cxypheny) thiourea

A technology of phenoxyphenyl and diisopropylaniline, which is applied in the field of preparation of thiourea organic compounds, can solve the problems of many reaction by-products, high raw material prices, high toxicity, etc., and achieves high total yield and low cost The effect of fewer energy and reaction steps

Inactive Publication Date: 2007-02-14
中国中化股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] The purpose of the present invention is to provide a method for preparing thiourea organic compounds with asymmetric structure suitable for industrial production, especially to provide a method for preparing difenuron, so as to solve the problem of high raw material prices in the prior art , high toxicity, many reaction by-products, high energy consumption, etc.

Method used

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  • Method for preparing 1-tert butyl-3-(2,6-diisopropyl-4-phenyl cxypheny) thiourea
  • Method for preparing 1-tert butyl-3-(2,6-diisopropyl-4-phenyl cxypheny) thiourea
  • Method for preparing 1-tert butyl-3-(2,6-diisopropyl-4-phenyl cxypheny) thiourea

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Experimental program
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Effect test

Embodiment 1

[0029] (1) Add 4-phenoxy-2,6-diisopropylaniline 4.2g (content 91%, 0.014mol), carbon disulfide 4g (content 99%, 0.052mol), triethylamine 5.3g to the reaction flask (content 99%, 0.052 mol) and toluene 10ml, stirred at 20~25 ℃ for about 14 hours, when the content of 4-phenoxy-2,6-diisopropylaniline in the raw material monitored by HPLC was less than 1%, the reaction ended. A yellow solid precipitated out in the reaction flask and was filtered. The filtrate was reserved for the next application; the filter cake was dried to obtain 6.2 g of solid as triethylamine dithio(4-phenoxy-2,6-diisopropylanilino)formate.

[0030] (2) Put the triethylamine dithio(4-phenoxy-2,6-diisopropylphenylamino)formate solid obtained in the previous step into the reaction flask, add 10ml tert-butylamine and 10ml triethylamine at 20~ Stir at 25°C for about 24 hours, and when the content of triethylamine dithio(4-phenoxy-2,6-diisopropylanilino)formate in the raw material monitored by HPLC is less than 1...

Embodiment 2

[0032] (1) Add 4-phenoxy-2,6-diisopropylaniline 21.0g (content 93%, 0.07mol), carbon disulfide 21.6g (content 99%, 0.28mol) and toluene 100ml in 250ml autoclave, After ammonia replacement, at 20-25°C, 8kg / cm 2 The reaction was continued under pressure with ammonia stirring for about 24 hours. When the content of 4-phenoxy-2,6-diisopropylaniline hydrochloride in the raw material monitored by HPLC was less than 1%, the reaction ended. A yellow ammonium dithio(4-phenoxy-2,6-diisopropylanilino)formate solid precipitated out of the reaction mixture.

[0033] (2) Put the yellow reaction mixture obtained in the previous step into a reaction flask, add 10ml of tert-butylamine and stir at 20-25°C for about 24 hours. The raw material dithio(4-phenoxy-2,6-diisopropyl When the ammonium salt content of anilino)formate is less than 1%, the reaction ends. Excess tert-butylamine and solvent toluene were removed by distillation under reduced pressure, which will be used in the next step; 40m...

Embodiment 3

[0035] (1) Add 23.7g (content 93%, 0.072mol) of 4-phenoxy-2,6-diisopropylaniline hydrochloride to the reaction flask, then add 20ml ammonia (25%) and 25ml water, Add 21.6 g of carbon disulfide (content 99%, 0.28 mol) dropwise under stirring, stir at 20-25°C for about 24 hours, and monitor the content of the raw material 4-phenoxy-2,6-diisopropylaniline hydrochloride by HPLC to be less than 1 %, the reaction ends. A yellow solid precipitated out in the reaction flask and was filtered. The filtrate was reserved for the next application; the filter cake was dried to obtain 25.9 g of solid as dithio(4-phenoxy-2,6-diisopropylanilino)ammonium formate.

[0036](2) Put the solid obtained in the previous step into a reaction flask, add 30 ml of tert-butylamine and stir at 20-25°C for about 24 hours. The raw material dithio(4-phenoxy-2,6-diisopropylbenzene When the amino) ammonium formate content is less than 1%, the reaction ends. Distill under reduced pressure to remove excess tert...

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Abstract

The present invention is process of preparing 1-tertbutyl-3-(2, 6-diisopropyl-4-phenoxyl phenyl) thiourea. The preparation process includes the following steps: 1. the reaction of 4-phenoxyl-2, 6- diisopropyl aniline or its salt, CS2 and one kind of organic alkali or inorganic alkali in solvent to produce corresponding 4- phenoxyl-2, 6-diisopropyl aniline dithio formate; and 2. the reaction of 4- phenoxyl-2, 6-diisopropyl aniline dithio formate and tert-butylamine inside organic solvent to produce 1-tertbutyl-3-(2, 6-diisopropyl-4-phenoxyl phenyl) thiourea. The preparation process of the present invention has less reaction steps, high total yield, simple operation, mild reaction condition and facile cheap material, and is suitable for industrial production.

Description

technical field [0001] The invention provides a preparation method of a thiourea organic compound with an asymmetric structure. Specifically, it relates to a method for preparing 1-tert-butyl-3-(2,6-diisopropyl-4-phenoxyphenyl) thiourea (Chinese common name: difenthiuron, English common name: Diafenthiuron , hereinafter referred to as the method of thifenuron). Background technique [0002] Difenuron is an organic thiourea insecticide and acaricide with an asymmetric structure developed by Ciba-Geigy in the 1980s. Its structure is as follows: [0003] [0004] Patent FR2465720 reports the synthesis and insecticidal and acaricidal activities of the compound. [0005] Patents FR2465720, BE888179, and EP210487 report the synthesis of isothiocyanate, 4-phenoxy-2,6-diisopropylaniline, from the reaction of 4-phenoxy-2,6-diisopropylaniline and thiophosgene A general preparation method for the reaction of phenyl phenyl isothiocyanate with tert-butylamine to prepare difenuron. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C335/18
Inventor 郭胜王英辉李艳娟于福强
Owner 中国中化股份有限公司
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