Method for preparing amide

A technology of amides and organic amines, applied in the field of amides and preparation of amides, can solve the problems of harsh reaction conditions, difficult purification, low yield, etc., and achieve the effects of short reaction time, simple reaction system and low reaction temperature

Active Publication Date: 2016-10-26
SHANGHAI INST OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Aiming at the above-mentioned technical problems in the prior art, the present invention provides a method for preparing amides. The method for preparing amides needs to solve the problems of high cost of synthesizing amide bonds, harsh reaction conditions and low yield in the prior art. , the technical problem of difficult purification

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  • Method for preparing amide

Examples

Experimental program
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Embodiment 1

[0027] Add 1.40g of triphenoxyphosphine in a 100mL three-necked flask, and vacuum 2 , add 5mL of acetonitrile, and slowly add 0.55mL of oxalyl chloride dropwise under magnetic stirring. At this time, the reaction is violent and a large amount of gas is released, and the reaction lasts for 10 minutes. Then add 0.61g of benzoic acid and 0.59mL of aniline, and react at room temperature for 0.5 hour. The reaction is tracked by TLC, quantified by column chromatography, and qualitatively by NMR. The productive rate of benzanilide is 94%, and the NMR figure is shown in the attached figure 1 .

Embodiment 2

[0029] Add 1.40 g of triphenoxyphosphine into a 100 mL three-necked flask, vacuumize and ventilate with N 2 , add 5mL of acetonitrile, and slowly add 0.55mL of oxalyl chloride dropwise under magnetic stirring. At this time, the reaction is violent and a large amount of gas is released, and the reaction lasts for 10 minutes. Then add 0.61g of benzoic acid and 0.71mL of benzylamine, react at room temperature for 0.5 hour, react with TLC follow-up, carry out purification and quantification with column chromatography, the productive rate of N-benzylbenzamide is 91%, and the NMR Qualitative, see attached NMR map figure 2 .

Embodiment 3

[0031] Add 1.40 g of triphenoxyphosphine into a 100 mL three-necked flask, vacuumize and ventilate with N 2 , add 5mL of acetonitrile, and slowly add 0.55mL of oxalyl chloride dropwise under magnetic stirring. At this time, the reaction is violent and a large amount of gas is released, and the reaction lasts for 10 minutes. Then add 0.86g of α-naphthoic acid and 0.71mL of benzylamine, react at room temperature for 0.5 hour, react with TLC follow-up, carry out purification and quantification with column chromatography, the productive rate of N-benzyl-α-naphthoamide is 75%, qualitative by NMR, see attached NMR image 3 .

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Abstract

The invention provides a method for preparing amide. The method includes weighing triphenyl phosphine oxide, oxalyl chloride, organic acid and organic amine according to a molar ratio of 1-5:1-5:1:0.3-4; adding the triphenyl phosphine oxide, the oxalyl chloride, the organic acid and the organic amine into a reaction vessel, stirring the triphenyl phosphine oxide, the oxalyl chloride, the organic acid and the organic amine in N2 environments and carrying out reaction on the organic acid and the organic amine in the presence of organic solvents at the reaction temperature of 10-40 DEG C for the reaction time of 0.5-5 hours to generate the corresponding amide. The method has the advantages that the triphenyl phosphine oxide is used as a novel carboxylic acid activating agent to promote synthesis of the amide, the method is low in reaction temperature and short in reaction time, and the triphenyl phosphine oxide which is the carboxylic acid activating agent is inexpensive, is easily available and can be recycled; only reaction byproducts CO and CO2 can be generated, and accordingly the method is high in atom utilization rate.

Description

Technical field: [0001] The invention belongs to the field of organic chemistry and relates to an amide, in particular to a method for preparing the amide. Background technique: [0002] The amide bond is one of the most important chemical functional groups in nature, and is the main component of proteins in organisms, widely present in natural products, pesticides and pharmaceutical molecules. According to market research, about 25% of the best-selling drug molecules contain amide bonds. It is because of the wide application of the amide bond that the research on its synthetic method is of great significance. The synthesis of the traditional amide bond is through the direct reaction of one molecule of carboxylic acid and one molecule of amine to produce one molecule of water at the same time. However, this method has high reaction temperature, low conversion rate and difficult purification. [0003] [0004] In order to avoid the above problems, in the synthesis of am...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02C07C233/65C07C233/64
CPCC07C231/02C07C233/65C07C233/64
Inventor 孙小玲蒋立雪牛凡凡喻静李天奇
Owner SHANGHAI INST OF TECH
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