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Synthesis process of N-chloromethyl-N-phenyl amino formyl chloride

A technology of phenylcarbamoyl and synthetic method, which is applied in the preparation of carbamic acid derivatives, chemical instruments and methods, and the preparation of organic compounds, can solve problems such as destruction and no related reports, and achieve high yield Effect

Inactive Publication Date: 2007-11-07
蒋亦清
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since carbon tetrachloride is a substance that destroys the atmospheric ozone layer, it is prohibited to use it as a solvent
For a long time, the replacement of carbon tetrachloride has been the focus of research, but the non-carbon tetrachloride solvent synthesis method of this product has not been reported so far.

Method used

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  • Synthesis process of N-chloromethyl-N-phenyl amino formyl chloride
  • Synthesis process of N-chloromethyl-N-phenyl amino formyl chloride

Examples

Experimental program
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Embodiment 1

[0023] Put 200ml dichloroalkane industrial product into a 500ml four-neck glass flask, add phosgene at 20℃~65℃ under stirring, and add 80gN-methylaniline dropwise at the same time, keep a certain light passing speed and dropping speed, phosgene :N-methylaniline=1.1~2.0:1.0 (molar ratio), after the addition, the temperature is raised to 60℃~70℃, and part of phosgene is added until the N-methylaniline is completely converted, and it will decrease after the end point Pressure desolventization, to 110 ℃, vacuum degree ≥ 0.09mpa after desolventization, directly transferred to a 250ml four-necked flask, and weighed, the product weight 128g, 98% content, 98.5% yield.

[0024] Heat the photochemical obtained above to 80℃~130℃, add 1g of the catalyst azoisobutyronitrile, or keep the temperature 130~60℃ under UV lamp, pass in the chlorine gas 53g, and gradually reduce the chlorination temperature from 80℃~ When the temperature is lowered from 130°C to 60-80°C, the chlorination is over, samp...

Embodiment 2

[0027] The dichloroethane was changed to ethyl acetate, and the feeding amount and method were the same as in Example 1 to obtain 150 g of product, with a content of 93.6% and a yield of 92%.

[0028] The solvent ethyl acetate can also be replaced by methyl acetate or butyl acetate.

Embodiment 3

[0030] In the phosgenation reaction, toluene was used as the solvent to replace the dichloroethane in Example 1, and the treatment was carried out in the same manner as in Example 1, to obtain 153 g of product with a content of 92.5% and a yield of 92.8%.

[0031] The above solvent toluene can also be replaced by benzene, xylene or chlorinated benzene.

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Abstract

The present invention relates to synthesis process of N-chloromethyl-N-phenyl amino formyl chloride. The technological process includes the chloroformylating reaction of N-methyl aniline and phosgene in solvent to obtain N-methyl-N-phenyl amino formyl chloride, and the subsequent chlorination reaction of the resultant solution directly or after eliminating solvent with introduced chlorine at 60-130 deg.c under the action of catalyst or ultraviolet ray to obtain the product. Or, N-chloromethyl-N-phenyl amino formyl chloride is prepared with N-methyl-N-phenyl formamide as the initial material and through chlorination reaction with introduced chlorine at 60-130 deg.c under the action of catalyst or ultraviolet ray to obtain the product. The present invention realizes no solvent synthesis, and has high conversion rate and high product yield.

Description

Technical field [0001] The invention relates to a method for synthesizing N-chloromethyl-N-phenylcarbamoyl chloride, an intermediate of Buprofezin. Background technique [0002] N-chloromethyl N-phenylcarbamoyl chloride is the main intermediate for the synthesis of insecticide Buprofezin. In the prior art, there are mainly two ways to synthesize N-chloromethyl N-phenylcarbamoyl chloride: [0003] 1. Photochemical chlorination synthesis method, specifically, N-methylaniline is phosgenated in a solvent (benzenes, substituted benzenes, ketones, esters, chlorinated alkanes, etc.) to generate N-methyl -N-phenylcarbamoyl chloride (photochemical), then desolventize, add carbon tetrachloride, under ultraviolet light or catalyst conditions, carry out methyl chlorination reaction, or use carbon tetrachloride as solvent after photochemical reaction Direct chlorination reaction, desolventize to obtain the target product; [0004] [0005] (chloride) [0006] 2. N...

Claims

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Application Information

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IPC IPC(8): C07C271/04C07C269/00
Inventor 蒋亦清
Owner 蒋亦清
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