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Preparation method of amide compound

A technology of dehydration and condensation of amide compounds, applied in the preparation of organic compounds, carboxylic acid amide preparation, chemical instruments and methods, etc., can solve the problems of high cost of coupling reagents, many chemical wastes, cumbersome procedures, etc., and achieve easy separation Purification, broad substrate range, and simple operation

Pending Publication Date: 2022-01-11
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing methods have problems such as high cost of coupling reagents, a lot of chemical waste, cumbersome procedures in industrial production, and difficult purification. In view of the increasing demand for amide products, it is urgent to develop an efficient, economical, environmentally friendly, and renewable. Coupling Reagents for Amide Production

Method used

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  • Preparation method of amide compound
  • Preparation method of amide compound
  • Preparation method of amide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] A kind of preparation method of amides compound, reaction formula is as follows:

[0025]

[0026] Specific steps are as follows:

[0027] Add diethylamine (10mmol), benzoic acid (30mmol), sodium hydroxide (30mmol), bromomethylsulfonyl fluoride (15mmol), and acetonitrile (25mL) into a 100mL pressure bottle, and reflux the reaction in an oil bath at 50°C 18h, after the reaction, add 30mL of 1M sodium hydroxide solution to the reaction solution, then extract 3 times with 20mL of ethyl acetate, wash the extract with 20mL of 1M hydrochloric acid solution, then add anhydrous sodium sulfate to dry and distill under reduced pressure, The white solid N,N-diethylbenzamide fluoride (1.41 g, 80% yield) was obtained.

[0028] The hydrogen spectrum data of the amide compounds obtained in the present embodiment are as follows: 1 H-NMH (500MHz, CDCl 3 )δ=7.40-7.36(m,5H),3.56(s,2H),3.26(s,2H),1.26(s,3H),1.11(s,3H).

Embodiment 2

[0030] A kind of preparation method of amides compound, reaction formula is as follows:

[0031]

[0032] Specific steps are as follows:

[0033] Add aniline (10mmol), o-trifluoromethylbenzoic acid (30mmol), sodium hydroxide (30mmol), bromomethylsulfonyl fluoride (15mmol), acetonitrile (25mL) into a 100mL pressure bottle, and place in an oil bath at 50°C Under reflux for 18 hours, after the reaction, add 30mL of 1M sodium hydroxide solution to the reaction solution, then extract 3 times with 20mL of ethyl acetate, wash the extract with 20mL of 1M hydrochloric acid solution, then add anhydrous sodium sulfate to dry and reduce Pressure distillation gave white solid N-phenyl-2-(trifluoromethyl)benzamide (2.20 g, 83% yield).

[0034] The hydrogen spectrum data of the amide compounds obtained in the present embodiment are as follows: 1 H-NMH (500MHz, DMSO-d 6 )δ=10.55(s,1H),7.85(d,J=7.6Hz,1H),7.80(t,J=7.3Hz,1H),7.73-7.70(m,4H),7.36(t,J=7.6 Hz,2H),7.12(t,J=7.3Hz,1H). 19 F-NM...

Embodiment 3

[0036] A kind of preparation method of amides compound, reaction formula is as follows:

[0037]

[0038] Specific steps are as follows:

[0039] Add L-valine ethyl ester (10mmol), benzoic acid (30mmol), sodium hydroxide (30mmol), bromomethylsulfonyl fluoride (15mmol), acetonitrile (25mL) to a 100mL pressure bottle, The reaction was refluxed in the bath for 18 hours. After the reaction, 30 mL of 1M sodium hydroxide solution was added to the reaction solution, and then extracted three times with 20 mL of ethyl acetate. The extract was washed with 20 mL of 1M hydrochloric acid solution, and then dried by adding anhydrous sodium sulfate. Distilled under reduced pressure to obtain white solid benzoyl-L-valine ethyl ester (2.17g, 87% yield, 99% ee).

[0040] The hydrogen spectrum data of the amide compounds obtained in the present embodiment are as follows: 1 H-NMR (500MHz, CDCl 3 )δ=7.81(d, J=7.3Hz, 2H), 7.50(t, J=7.3Hz, 1H), 7.44(t, J=7.5Hz, 2H), 6.68(d, J=7.7Hz, 1H) ,4.76...

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Abstract

The invention relates to a preparation method of an amide compound. The method comprises the following steps: by taking amine and carboxylic acid as raw materials and bromomethylsulfonyl fluoride as a coupling reagent, carrying out dehydration condensation reaction in the presence of alkali and a solvent, and finally separating and purifying to obtain the amide compound. The preparation method has the characteristics of simplicity in operation, low preparation cost, easiness in separation and purification of products and the like, is wide in substrate range, can be used for condensation of amino acids and synthesis and modification of bioactive molecules, and is expected to be used for large-scale synthesis of amides.

Description

technical field [0001] The invention belongs to the technical field of preparing carboxylic acid amides from carboxylic acids or their esters, anhydrides or halides by reacting with ammonia or amines, and relates to a preparation method of amide compounds. Background technique [0002] As one of the most prevalent and important functional groups in organic chemistry, amide bonds not only appear as key linkers in polypeptides, proteins, bioactive compounds, agrochemicals, and polymers, but also widely exist in about 25% of drugs on the market middle. Although there have been many methods for the synthesis of amides from alcohols, aldehydes, and nitriles, the direct dehydration condensation of amines and carboxylic acids is still the most straightforward method. The direct condensation of amines and carboxylic acids often requires harsh conditions. In order to avoid these problems, a variety of coupling reagents have been developed to mediate the dehydration condensation of a...

Claims

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Application Information

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IPC IPC(8): C07C231/02C07C233/65C07C233/83C07C269/06C07C271/22C07D213/82C07C233/07C07C233/15C07C233/25C07C233/66C07C233/58C07C233/87
CPCC07C231/02C07C269/06C07D213/82C07C2601/02C07C233/65C07C233/83C07C271/22C07C233/07C07C233/15C07C233/25C07C233/66C07C233/58C07C233/87
Inventor 秦华利吴启新
Owner WUHAN UNIV OF TECH
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