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Preparation method of 3-(N-methyl-N-phenyl)aminoacrolein

A technology of aminoacrolein and methylaniline, which is applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve the problems of high raw material prices, long reaction time, cumbersome post-processing, etc., and reduce the generation of impurities , improve quality, and reduce the effect of three wastes pollution

Inactive Publication Date: 2017-02-22
JINTAN DEPEI CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] 2. Using N-methylformanilide, vinyl n-butyl ether and triphosgene as raw materials, such as US 7091382; that is, N-methylformanilide, vinyl n-butyl ether and triphosgene react in chlorobenzene , the method uses the three wastes produced after the triphosgene reaction is toxic and unfavorable for environmental protection
[0006] 3. Using N-methylaniline, propynyl alcohol and manganese dioxide as raw materials, such as PCT Int.Appl., 2006090256, 31Aug 2006; that is, N-methylaniline, propynyl alcohol and manganese dioxide react in dioxane , the reaction time of this method is long, and the post-treatment is cumbersome, and the price of raw materials used is relatively high

Method used

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  • Preparation method of 3-(N-methyl-N-phenyl)aminoacrolein

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Put 100g of tetramethoxypropane and 58.8g of N-methylaniline in a 1L reaction flask in turn, stir for 10 minutes, control the internal temperature below 30°C, add 22g of 20% hydrochloric acid dropwise, keep the temperature at 24°C and stir for 2.5 hours. Add 200 g of toluene, add 20% liquid caustic soda to control the temperature below 30°C to make the pH of the water layer 6-7, stand still for layering, extract the water layer with toluene, combine the organic layers, wash three times with saturated brine, stand still to separate the water layer. The organic layer is first reduced in pressure to recover the solvent, and then the 60-70°C / 40mmHg fraction is collected to obtain 83.1 g of 3-(N-methyl-N-phenyl)amino acrolein with a content of 99.6%.

Embodiment 2

[0027] Put 100g of tetramethoxypropane and 62g of N-methylaniline in a 1L reaction flask in sequence, stir for 10 minutes, control the internal temperature below 30℃, add 22g of 20% hydrochloric acid dropwise, keep warm and stir for 2.5 hours at about 25℃, add 200g of toluene, add 20% liquid caustic soda to control the temperature below 30℃ to make the pH of the water layer 6~7, stand still for layering, extract the water layer with toluene, combine the organic layers, wash three times with saturated brine, stand still to separate the water layer, organic The layer was firstly decompressed to recover the solvent, and then the 60-70°C / 40mmHg fraction was collected to obtain 83.5g of 3-(N-methyl-N-phenyl)amino acrolein with a 99.5% content.

Embodiment 3

[0029] Put 100g of tetramethoxypropane and 65.4g of N-methylaniline in a 1L reaction flask in turn, stir for 10 minutes, control the internal temperature below 30°C, add 22g of 20% hydrochloric acid dropwise, keep the temperature at 26°C and stir for 2.5 hours. Add 200 g of toluene, add 20% liquid caustic soda to control the temperature below 30°C to make the pH of the water layer 6-7, stand still for layering, extract the water layer with toluene, combine the organic layers, wash three times with saturated brine, stand still to separate the water layer. The organic layer is firstly decompressed to recover the solvent, and then the 60-70° C. / 40 mmHg fraction is collected to obtain 83.4 g of 3-(N-methyl-N-phenyl)amino acrolein with a content of 99.5%.

[0030] Example 2 is a preferred trial method.

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Abstract

The invention relates to the technical field of pharmaceutical intermediates, in particular to a preparation method of 3-(N-methyl-N-phenyl)aminoacrolein. The preparation method comprises the following steps that tetramethoxypropane and N-methylaniline are put into a reaction flask, and after stirring is conducted for 10 min, diluted hydrochloric acid is dropwise added; after diluted hydrochloric acid is dropwise added completely, stirring is conducted for 2.5 h at the temperature of 24 DEG C to 26 DEG C; methylbenzene is added, and caustic soda liquid is dropwise added at 30 DEG C or below to regulate the pH value to be 6-7; standing is conducted for layering, a water layer is extracted with methylbenzene, organic layers are mixed, and washing is conducted three times with a saturated salt solution; standing is conducted for layering, a solvent in the organic layer is recycled by reducing pressure, 60-70-DEG C 40-mmHg distillates are collected, and then the product is obtained. According to the preparation method, expensive N-methylformanilide, n-butyl vinyl ether and propargyl alcohol are not used as raw materials, and therefore the cost is reduced; due to the fact that conventional solvents such as acetonitrile and chlorobenzene and poisonous substances such as triphosgene are not used, three waste pollution is reduced, and the reaction yield is increased; in the synthesis process, reacting is conducted at the environment temperature, the operation process is simplified, impurity generation is reduced, the quality of the product is improved, and the reaction yield is increased.

Description

Technical field [0001] The invention relates to the technical field of pharmaceutical intermediates, in particular to a preparation method of 3-(N-methyl-N-phenyl)amino acrolein. Background technique [0002] 3-(N-Methyl-N-phenyl)amino acrolein is a raw material for pharmaceuticals and chemicals, such as the synthesis of fluvastatin sodium [0003] The research on the synthesis of 3-(N-methyl-N-phenyl)amino acrolein has been continuously improved and improved in the past ten years. The current synthesis methods are mainly: [0004] 1. Take N-methyl formanilide, vinyl ethyl ether and oxalyl chloride as raw materials, such as Journal of Organic Chemistry, 75(22), 7514-7518; 2010; namely, N-methyl formanilide, vinyl ethyl ether and grass The acid chloride is reacted in acetonitrile at -10°C. All solvents used in this method are toxic, and the reaction conditions are harsh, and the raw materials used are expensive. [0005] 2. Take N-methyl formanilide, vinyl n-butyl ether and triphosgen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C221/00C07C223/02
CPCC07C221/00
Inventor 储著玮岳波叶荫其他发明人请求不公开姓名
Owner JINTAN DEPEI CHEM
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