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Novel method for hydrolyzing nitrile group to acylamino

A technology of amide group and new method, which is applied in the field of hydrolysis of nitrile group to amide group, which can solve the problems of easy side reactions, harsh reaction conditions, and unfriendly environment, and achieves cheap and easy-to-obtain catalysts, short reaction time, and high selectivity Effect

Inactive Publication Date: 2013-10-09
YANGZHOU UNIV
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Problems solved by technology

However, these methods all have the disadvantages of long reaction time, side reactions, harsh reaction conditions, and environmental unfriendliness.

Method used

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  • Novel method for hydrolyzing nitrile group to acylamino
  • Novel method for hydrolyzing nitrile group to acylamino

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Embodiment Construction

[0019] 1. Reaction steps (take the conversion of benzonitrile into benzamide as an example):

[0020] Add 2g of benzonitrile, 0.3g of N,N'-di-n-pentylbenzimidazolium bromide and 100ml of deionized water in a 25mL round-bottomed flask, and add 0.1g of DBU (1,8 -diazabicyclo[5.4.0]undec-7-ene), heated to 80°C, kept at reflux for 2.5h, after the reaction, most of the water was evaporated and thin-layer chromatography separated benzamide amine 1.9 g.

[0021] In the thin layer chromatography adopted, a mixture of cyclohexane and ethyl acetate was used as an eluent, and the mixing volume ratio of cyclohexane and ethyl acetate was 10:1.

[0022] Different types of amide compounds can be obtained by replacing benzonitrile with different substituted nitrile compounds.

[0023] General reaction formula of the present invention is:

[0024]

[0025] 2. Product identification:

[0026] The experimental data of the different substituted amides produced by the process of the present...

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Abstract

The invention relates to a novel method for hydrolyzing nitrile grouping to acylamino. The method comprises the following steps: adding a nitrile compound, N,N'-Di-n-amyl bromide benzimidazole,1,8-Diazabicyclo[5.4.0]undec-7-ene with a mol ratio of 1:0.05:0.05 into water, uniformly stirring, heating and carrying out heat preservation on reaction liquid until the reaction of the reaction liquid is finished, removing water, and performing thin-layer chromatography separation on residues to obtain amide compounds. According to the method provided by the invention, such original defects as long reaction time, liability to generation of side reactions, harsh reaction conditions and environmental pollution are overcome. The method provided by the invention is moderate in conditions, high in selectivity and short in reaction time, no traditional strong acid or strong alkali is used as a catalyst, the nitrile grouping is completely converted to the acylamino, no further hydrolysis to produce carboxyl by-products is generated and the catalyst is cheap and easy to obtain.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a new method for hydrolyzing nitrile groups into amide groups. Background technique [0002] Amide compounds are an important class of organic compounds. As intermediates or final products, they are widely used in the fields of organic synthesis, pharmaceutical synthesis, pesticides, papermaking and functional materials, especially in the production of fine chemicals. Very important low. The synthesis of amides is an important reaction in organic chemistry. [0003] Before the present invention, the common synthetic method is to convert carboxylic acid into carboxylic acid derivatives such as acid chlorides, esters or acid anhydrides at first, and then generate corresponding amide compounds by ammonolysis reaction of these carboxylic acid derivatives. There are also reports of synthesis of amides by microwave method or enzyme-catalyzed method. However, these methods...

Claims

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Application Information

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IPC IPC(8): C07C231/06C07C233/65C07C237/30
Inventor 景崤壁谭晓东丁兆兵
Owner YANGZHOU UNIV
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