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Method for synthesizing diphenyl urea and derivative of diphenyl urea

A technology of diphenylurea and synthesis method, which is applied in the preparation of urea derivatives, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of low yield, heavy pollution and high temperature, and achieve high utilization rate of raw materials, Good product quality and less pollution

Inactive Publication Date: 2015-04-15
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] In order to solve the above problems, i.e. heavy pollution, low yield, high temperature and other problems, the invention provides a simple method with less pollution, mild reaction conditions and high yield to synthesize N, N'-diphenylurea

Method used

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  • Method for synthesizing diphenyl urea and derivative of diphenyl urea
  • Method for synthesizing diphenyl urea and derivative of diphenyl urea
  • Method for synthesizing diphenyl urea and derivative of diphenyl urea

Examples

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Effect test

example 1

[0031] Example 1 is the methyl chloroformate method reported in the literature. Add aniline 9.32g and tri-n-butylamine 27.75g successively in a 250mL round-bottomed flask, add methyl chloroformate 14.18g dropwise under ice-water cooling and stirring, and heat to 120 Make it reflux at ℃, react for 3 hours, cool to room temperature, add 50mL of absolute ethanol, and slowly pour into 250mL of distilled water under stirring, forming a khaki flocculent precipitate. Stand overnight at 4°C, filter with suction the next day, and wash the precipitate with water three times. Recrystallized twice from absolute ethanol and dried at 100°C for 2 hours to obtain a solid with a yield of 90.50%.

example 2

[0033] Add 30.00g of dichloromethane, 1.18g of triethylamine, and 0.99g of aniline to a 100mL four-neck flask in sequence. According to the molar ratio of aniline to benzyl chloroformate is 1.0:1.1, add benzyl chloroformate dropwise under stirring at 0-10°C Esters 2.00g, continue to stir at room temperature for 1h after the dropwise addition is completed, add an equal amount of ethyl acetate as a solvent to the reaction solution, stir, filter to remove triethylamine hydrochloride, add saturated aqueous sodium bicarbonate solution to the filtrate, and stir for 15min , standing for stratification, extraction, washing with water for 3 to 5 times, taking the organic layer, adding anhydrous magnesium sulfate to dry, filtering, and distilling off the organic solvent under reduced pressure to obtain a solid, which is then separated by column chromatography to obtain a product with a purity of 95.69% , and the yield was 91.67%.

example 3

[0035] Add 30.00g of dichloromethane, 1.18g of triethylamine, and 1.31g of p-methoxyaniline to a 100mL four-necked flask in sequence. Add 2.00 g of benzyl chloroformate dropwise under stirring at ℃, continue to stir at room temperature for 5 hours after the dropwise addition is completed, add an equal amount of ethyl acetate as a solvent to the reaction solution, stir, remove triethylamine hydrochloride by filtration, and add saturated Aqueous sodium bicarbonate solution, stirred for 15 minutes, allowed to stand for stratification, extracted, washed 3 to 5 times with water, took the organic layer, added anhydrous magnesium sulfate to dry, filtered, and distilled off the organic solvent under reduced pressure to obtain a solid, which was then subjected to column chromatography After separation, the purity of the product obtained was 99.63%, and the yield was 81.38%.

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Abstract

The invention discloses a method for synthesizing diphenyl urea and a derivative of the diphenyl urea, and belongs to the field of organic synthesis. The method comprises the following steps: preparing the target products, namely N, N'-diphenyl urea and the derivative of the diphenyl urea by taking aniline or substituted aniline and benzyl chloroformate as raw materials under the existence of an organic solvent and alkali. Compared with a conventional phosgenation method, the method disclosed by the invention has the advantages that diphenyl urea obtained by the method does not contain toxic phosgene, so that pollution to the environment is low. Compared with an industrial urea method, the method disclosed by the invention has the advantages that the raw material utilization rate is high, and the problem of production of waste gas is solved. Compared with a conventional methylclhlorofonmate method, the method disclosed by the invention has the advantages that no heating reflux is needed, and the characteristics of mild reaction temperature, high yield and high product quality are achieved.

Description

technical field [0001] The invention relates to a synthesis method of a pharmaceutical intermediate diphenylurea and derivatives thereof, belonging to the field of organic synthesis. Background technique [0002] N, N'-diphenylurea (N, N'-diphenylurea, DPU) is an important organic pharmaceutical intermediate, mainly used in the preparation of sulfa drugs. Its molecular structure contains carbonyl group and aniline group, which can undergo alcoholysis reaction to synthesize methyl anilinate, and is an important intermediate in the clean process of non-phosgene synthesis of diphenylmethane diisocyanate. At the same time, N, N'-diphenylurea has a good application prospect in the agricultural field, and is a good herbicide, insecticide and plant growth regulator. N, N'-diphenylurea has the ability to promote cell division, The effects of growth, quality improvement, yield increase and early harvest are superior to purine series plant growth regulators. [0003] According to ex...

Claims

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Application Information

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IPC IPC(8): C07C275/28C07C275/34C07C275/30C07C273/18
Inventor 宋国强秦枫曹引梅冯筱晴吕小兵
Owner CHANGZHOU UNIV
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