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Alpha-cyaniding method of N-arylmethylaniline

A technology of arylmethylaniline and trimethylsilyl cyanide, which is applied in the field of organic chemical synthesis, can solve problems such as unfavorable industrial production, metal ion pollution of products, inapplicability to mass production, etc., achieve high yield, save industrial costs, The effect of a short reaction cycle

Inactive Publication Date: 2019-06-25
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] (1) The reaction time of this method is too long, thereby increases production cost, is unfavorable for suitability for industrialized production
[0005] (2) This reaction uses a complex of vanadium as a catalyst. Due to the high cost of the catalyst, it is not suitable for industrial mass production, and it is easy to cause metal ion pollution of the product

Method used

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  • Alpha-cyaniding method of N-arylmethylaniline
  • Alpha-cyaniding method of N-arylmethylaniline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] A kind of α-cyanidation method of N-arylmethylaniline, its concrete steps are as follows:

[0024] (1) Take N-benzylaniline as raw material, N-benzylaniline mmol: TMSCN mmol: DDQ mmol: the ratio of ethyl acetate milliliter ratio 1: 2.0: 1.2: 4, first add in the reactor N-benzylaniline (91.6mg, 0.5mmol), was added solvent ethyl acetate (2mL), under stirring, then added trimethylsilyl cyanide (125μL, 1.0mmol), DDQ (136.2mg, 0.6mmol), and After finishing, at room temperature, the oxidative cyanation reaction was carried out with continuous stirring for 5 hours.

[0025] (2) After step (1) is completed, add saturated sodium thiosulfate solution to the reaction solution prepared in step (1) to quench, extract with ethyl acetate, combine organic phases, and dry over anhydrous magnesium sulfate. Suction filtration, rotary evaporation to concentrate the organic phase, the organic phase was purified by silica gel column chromatography, and eluted with the eluent, and the efflue...

Embodiment 2

[0028] A kind of α-cyanidation method of N-arylmethylaniline, its concrete steps are as follows:

[0029] (1) Take N-benzylaniline as raw material, N-benzylaniline mmol: TMSCN mmol: DDQ mmol: the ratio of DMF milliliter ratio 1: 2.0: 1.2: 4, add N- Benzylaniline (91.6mg, 0.5mmol), add the solvent DMF (2mL), under stirring, then add trimethylsilyl cyanide (125μL, 1.0mmol), DDQ (136.2mg, 0.6mmol) successively, after addition, at room temperature Under continuous stirring, the oxidative cyanation reaction was carried out for 5 hours.

[0030] (2) After step (1) is completed, add saturated sodium thiosulfate solution to the reaction solution prepared in step (1) to quench, extract with ethyl acetate, combine organic phases, and dry over anhydrous magnesium sulfate. Suction filtration, rotary evaporation to concentrate the organic phase, the organic phase was purified by silica gel column chromatography, and eluted with the eluent, and the effluent of the silica gel column chromat...

Embodiment 3

[0033] A kind of α-cyanidation method of N-arylmethylaniline, its concrete steps are as follows:

[0034] (1) Take N-benzylaniline as raw material, N-benzylaniline mmol: TMSCN mmol: DDQ mmol: the ratio of acetonitrile milliliter ratio 1: 2.0: 1.2: 4, add N-benzylaniline earlier in the reactor Benzylaniline (91.6mg, 0.5mmol), add the solvent acetonitrile (2mL), under stirring, then add trimethylsilyl cyanide (125μL, 1.0mmol), DDQ (136.2mg, 0.6mmol) successively, after addition, at room temperature Under continuous stirring, the oxidative cyanation reaction was carried out for 5 hours.

[0035] (2) After step (1) is completed, add saturated sodium thiosulfate solution to the reaction solution prepared in step (1) to quench, extract with ethyl acetate, combine organic phases, and dry over anhydrous magnesium sulfate. Suction filtration, rotary evaporation to concentrate the organic phase, the organic phase was purified by silica gel column chromatography, and eluted with the elu...

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Abstract

An alpha-cyaniding method of N-arylmethylaniline is disclosed. According to the method, a finished product is obtained through a simple process of concentrating and purifying after reaction of variousN-arylmethylaniline derivatives as raw materials, trimethylsilyl cyanide as a cyanating agent and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone as an oxidant in a solvent. A new synthesis method is provided for solving the deficiencies of the existing oxidative cyanation process of N-arylmethylaniline. The method adopts the 2,3-dichloro-5,6-dicyano-1,4-benzoquinone which is low in price, low in toxicity and easily available as the oxidant, is free from metal ion catalysis, and efficiently realizes oxidative cyanation of various N-arylmethylaniline and the trimethylsilyl cyanide. The method disclosed by the invention is simple in process, safe in preparation reaction production, easy to operate, short in reaction time and beneficial to industrialization.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a method for synthesizing α-aminonitrile by α-cyanation of N-arylmethylaniline. Background technique [0002] As an important conversion group in organic synthesis, cyano group can be used as the precursor of many other functional groups. In the pharmaceutical industry, cyano groups are widely used in the structural modification of small molecule drugs, and the strategy of substituting cyano groups has become one of the important synthetic strategies for compound structure optimization. α-Aminonitriles can be used to construct biologically active compounds and functional materials, such as α-aminocarbonyl compounds, α-amino acids, o-diamines, imidazoles, etc. The method of hydrolyzing α-aminonitrile to generate α-amino acid is the most direct method in laboratory and industry at present. [0003] There are few reports on the oxidative cyanation of...

Claims

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Application Information

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IPC IPC(8): C07C253/00C07C255/43C07C255/42C07D333/24C07D307/54
Inventor 熊燕虞淑晨刘庆
Owner CHONGQING UNIV
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