Synthetic method for diaryl urea compound

A technology for diarylurea and aniline compounds, which is applied in the field of synthesis of diarylurea compounds, can solve the problems of difficult purification of products, harsh reaction conditions of diarylureas, etc., and achieves short reaction time, convenient post-processing, simple method effect

Inactive Publication Date: 2014-12-17
WENZHOU UNIVERSITY
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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 propose a synthesis method for the amidation reaction of a tertiary amine as a catalyst and an acid-binding agent in view of the relatively harsh reaction conditions of diaryl urea in the current production process, and the defects such as difficult purification of the product

Method used

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  • Synthetic method for diaryl urea compound
  • Synthetic method for diaryl urea compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Take 2.79 g of aniline and 2.97 g of triphosgene in a 250 mL three-necked flask, add 40 mL of dichloromethane, add 3.03 g of triethylamine dropwise in an ice bath, react at room temperature after the dropwise addition, and track and detect with TLC. The reaction is complete in about 1 hour. 35 mL of dichloromethane solvent was recovered by distillation, the residue was washed with 20 mL of water, filtered, and the filter cake was dried to obtain 3.08 g of N,N'-diphenylurea solid product, yield 97%, melting point m.p. 245.0-245.4 °C, Purity 98.4% (HPLC)

Embodiment 2

[0029] Take 2.79 g of aniline and 2.97 g of triphosgene in a 250 mL three-neck flask, add 40 mL of tetrahydrofuran, add 3.50 g of tri-n-propylamine dropwise under ice bath, react at room temperature after the dropwise addition, and track and detect with TLC. After 1 h, the reaction is complete, and the solvent is recovered by distillation Tetrahydrofuran was 37 mL, the residue was washed with 20 mL of water, filtered, and the filter cake was dried to obtain 3.02 g of N,N'-diphenylurea solid product, yield 95%, melting point m.p. 245.0-245.4 °C, purity 97.8% ( HPLC).

Embodiment 3

[0031] Take 3.21 g of 2-methylaniline and 2.97 g of triphosgene in a 250 mL three-necked flask, add 50 mL of ethyl acetate, add 3.03 g of triethylamine dropwise under ice-cooling, react at room temperature after the dropwise addition, and track and detect with TLC for 2 h After the reaction was complete, the ethyl acetate solvent was recovered by distillation. The residue was washed with 20 mL of water, filtered, and the filter cake was dried to obtain 3.52 g of 1,3-di-o-toluene urea as a solid. Ethanol was recovered by distillation with a yield of 98% and a melting point of 258.4- 258.9 °C, 98.5% purity (HPLC).

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Abstract

The invention discloses a synthetic method for a diaryl urea compound. The method comprises the following steps: an aniline compound, bis (trichloromethyl)carbonate and a tertiary amine compound, expressed in the formula II, are reacted at the room temperature in a reaction solution, and are tracked and detected by TLC (Thin Layer Chromatography) till the reaction is totally finished; and the diaryl urea compound which is expressed in the formula I can be prepared by aftertreatment of the reaction liquid . The method adopts triphosgene as an acylation reagent, and adopts the tertiary amine compound as a catalyst and acid-binding agent, so that the reaction time is short, the reaction is generally finished within 1-2 hours, the conversion rate of raw materials achieves 100%, the product yield is high above 95%, the aftertreatment is convenient, and the purity is high.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing diaryl urea compounds. (2) Background technology [0002] Diaryl urea is an important class of organic synthesis intermediates, which can be used to synthesize drugs for treating diabetes and analgesia, as well as intermediates for antioxidants, herbicides and insecticides in gasoline. Since the discovery and isolation of urea cytokinins such as diphenylurea (DPU), which have the activity of promoting plant cell division, artificially synthesized urea compounds have appeared one after another. In 1951, Butchar and Todd first reported the herbicidal activity of methuron. Since then, many varieties of urea herbicides have appeared, becoming an important class of herbicides. Substituted urea herbicides have attracted people's attention due to their advantages of high efficiency, broad spectrum and low toxicity. In recent years, the development and application of substituted urea compounds has develo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C273/18C07C275/28C07C275/30
Inventor 熊静周书光李大帅姚婷易际埕
Owner WENZHOU UNIVERSITY
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