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Preparation method of 3-oxo-N-(4-trifluoromethylphenyl) butylamide

A technology of trifluoromethylphenyl and trifluoromethylaniline, which is applied in the field of preparation of 3-oxo-N-butyramide, can solve the problems of unfavorable industrial production, high cost, and large solvent toxicity coefficient, and achieve cost Low, less by-products, the effect of shortening the reaction time

Pending Publication Date: 2021-03-09
SHANGHAI INST OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The solvent used in its research has a large toxicity coefficient and high cost, which is not conducive to industrial production

Method used

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  • Preparation method of 3-oxo-N-(4-trifluoromethylphenyl) butylamide
  • Preparation method of 3-oxo-N-(4-trifluoromethylphenyl) butylamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Put 120g of ethyl acetoacetate into a 1000ml dry and clean four-necked bottle, start the mechanical stirring device, then add 300g of p-trifluoromethylaniline and 0.27g of sodium methoxide successively, and vacuumize N 2 After protection, slowly heat to an internal temperature of 80° C., and keep the reaction for 1 hour. Then, the temperature was raised at a rate of 10°C per hour, and the temperature was raised to 100°C in 2.5 hours, and the temperature was maintained for 20 hours, and the distilled ethanol was received. Stop heating and cool down naturally, then slowly heat and pressurize to concentrate and recover the solvent. The residue is the product, and the purity of the 3-oxygen-N-(4-trifluoromethylphenyl) butyramide obtained in the present embodiment is detected by HPLC, see figure 1 , calculated according to the peak area normalization method, the purity of the 3-oxo-N-(4-trifluoromethylphenyl)butyramide prepared in this example is 94.6%.

Embodiment 2

[0024] Put 120g of ethyl acetoacetate into a 1000ml dry and clean four-neck bottle, start the mechanical stirring device, then add 575g of p-trifluoromethylaniline and 0.27g of tri-n-butylamine in turn, vacuumize N 2 After protection, slowly heat to an internal temperature of 80° C., and keep the reaction for 1 hour. Then the temperature was raised at a rate of 10° C. per hour, and the temperature was raised to an internal temperature of 120° C. in 2.5 hours, and the reaction was kept for 15 hours, and the distilled ethanol was received. Stop heating and cool down naturally, then slowly heat and pressurize to concentrate and recover the solvent. The residue is the product with a purity of 98.2%.

Embodiment 3

[0026] Put 120g of ethyl acetoacetate into a 1000ml dry and clean four-neck bottle, start the mechanical stirring device, then add 100g of p-trifluoromethylaniline and 0.27g of N-methylpyrrolidone in sequence, and vacuumize N 2 After protection, slowly heat to an internal temperature of 80° C., and keep the reaction for 1 hour. Then the temperature was raised at a rate of 10° C. per hour, and the temperature was raised to an internal temperature of 140° C. in 2.5 hours, and the temperature was maintained for 10 hours, and the distilled ethanol was received. After the heat preservation is over, the ethanol in the receiving tank is recovered. Stop heating and cool down naturally, then slowly heat and pressurize to concentrate and recover the solvent. The residue is the product with a purity of 96.09%.

[0027] Visible by above-mentioned implementation process, the present invention has abandoned special reaction solvent, by adding excessive reaction raw material is solvent, an...

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Abstract

The invention relates to a preparation method of 3-oxo-N-(4-trifluoromethylphenyl) butylamide, wherein the preparation method comprises the steps: carrying out amidation reaction on ethyl acetoacetateand p-trifluoromethylaniline to obtain 3-oxo-N-(4-trifluoromethylphenyl) butylamide, wherein in the reaction process, excessive p-trifluoromethylaniline is used as a solvent, and a catalyst adopted in the reaction process is an organic base catalyst. Compared with the prior art, the preparation method has the advantages that ethyl acetoacetate and p-trifluoromethylaniline are subjected to amidation reaction, and the product 3-oxo-N-(4-trifluoromethylphenyl) butylamide is obtained through post-treatment, wherein the synthesis operation of the 3-oxo-N-(4-trifluoromethylphenyl) butylamide is simple, the cost is low, the yield is high, the use of volatile toxic organic solvents and the emission of waste gas are avoided, and the process route is green and environment-friendly; and the obtainedproduct has few impurities, the target product has high purity, the raw materials are easy to recycle, the post-treatment operation is simple, the reaction time is shortened, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of preparation of pharmaceutical intermediates, in particular to a preparation method of 3-oxo-N-(4-trifluoromethylphenyl)butyramide. Background technique [0002] Teriflunomide (teriflunomide), the chemical name is (Z)-2-cyano-3-hydroxy-N-(4-trifluoromethylphenyl)-2-butenamide, teriflunomide is produced by Sano It was developed by Fei-Aventis and was approved by the FDA for marketing on September 12, 2012. It is mainly used for the treatment of multiple sclerosis (MS). It can significantly improve central nervous system diseases and reduce the recurrence rate. Compared with existing drugs, teriflunomide is safe and will not cause infection rise or tumor occurrence, so it is an ideal treatment for recurrent multiple Drugs for sexual sclerosis have strong competitiveness and good prospects for clinical application. Multiple sclerosis is a chronic, inflammatory, demyelinating central nervous system disease that can ca...

Claims

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Application Information

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IPC IPC(8): C07C235/80C07C231/02
CPCC07C231/02C07C235/80
Inventor 汪忠华李云芳吴范宏胡银杰陈秀萍冉剑雄王祥聪邵海兵
Owner SHANGHAI INST OF TECH
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