Method for N, N-dialkylaniline cyanation reaction

A technology of dialkylaniline and cyanation reaction, applied in the field of N, can solve the problems of increased production cost, large environmental pollution, and relatively expensive price, and achieve the effect of low production cost, small environmental pollution, and good market application prospects

Inactive Publication Date: 2015-06-03
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] (1) adopt ruthenium trichloride as catalyst in the above-mentioned method, and price is more expensive, makes production cost increase, and bigger to environmental pollution
[0005] (2) the used cyanide reagent sodium cyanide or potassium cyanide of above-mentioned method has highly toxic
[0006] (3) The above reactions generally need to be heated to reflux, and additional heat energy needs to be provided for the reaction

Method used

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  • Method for N, N-dialkylaniline cyanation reaction
  • Method for N, N-dialkylaniline cyanation reaction
  • Method for N, N-dialkylaniline cyanation reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] A kind of N, the method for N-dialkylaniline cyanation reaction, its concrete steps are as follows:

[0024] (1) With N,N-dimethylaniline A1 as raw material, bis(trifluoroacetoxy) iodobenzene as oxidizing agent, trimethylsilylcyanide as cyanating agent, anhydrous Na 2 SO 4 As an additive, 1,2-dichloroethane is a solvent, according to N, N-dimethylaniline A1 millimole: bis(trifluoroacetoxy) iodobenzene millimole: trimethylsilylcyanide millimole: additive without Water Na 2 SO 4 The ratio of mmoles: milliliters of solvent is the ratio of 1.0: 1.0: 2.0: 0.5: 6.0, and bis(trifluoroacetoxy) iodobenzene (215.0mg, 0.5mmol) and 1,2-dichloro Ethane (3.0mL), then added trimethylsilyl cyanide (99.2mg, 1.0mmol) under stirring, stirred for 40 minutes under ice bath, and then added anhydrous Na 2 SO 4 (36.0mg, 0.25mmol) and N, N-dimethylaniline A1 (61.0mg, 0.5mmol), after the addition is complete, continue stirring at this temperature for 1 hour to prepare N, N-dialkylaniline cy...

Embodiment 2

[0029] A kind of N, the method for N-dialkylaniline cyanation reaction, its concrete steps are with embodiment 1, wherein:

[0030] (1) With N,N-dimethylaniline A1 as raw material, bis(trifluoroacetoxy) iodobenzene as oxidizing agent, trimethylsilylcyanide as cyanating agent, anhydrous Na 2 SO 4 As an additive, 1,2-dichloroethane is a solvent, according to N, N-dimethylaniline A1 millimole: bis(trifluoroacetoxy) iodobenzene millimole: trimethylsilylcyanide millimole: additive without Water Na 2 SO 4 The ratio of millimoles: solvent milliliters is 1.0: 2.5: 2.0: 0.5: 6.0, and bis(trifluoroacetoxy) iodobenzene (538.0mg, 1.25mmol) and 1,2-dichloro Ethane (3.0mL), then added trimethylsilyl cyanide (99.2mg, 1.0mmol) under stirring, stirred for 40 minutes under ice bath, and then added anhydrous Na 2 SO 4 (36.0mg, 0.25mmol) and N, N-dimethylaniline A1 (61.0mg, 0.5mmol), after the addition is complete, continue stirring at this temperature for 1 hour to prepare N, N-dialkylanili...

Embodiment 3

[0033] A kind of N, the method for N-dialkylaniline cyanation reaction, its concrete steps are with embodiment 1, wherein:

[0034] (1) With N,N-dimethylaniline A1 as raw material, bis(trifluoroacetoxy) iodobenzene as oxidizing agent, trimethylsilylcyanide as cyanating agent, anhydrous Na 2 SO 4 As an additive, 1,2-dichloroethane is a solvent, according to N, N-two. Methylaniline A1 mmoles: two (trifluoroacetoxy) iodobenzene mmoles: trimethylsilylcyanide mmoles: additive Anhydrous Na 2 SO 4 The ratio of mmoles: milliliters of solvent is 1.0: 1.5: 1.5: 0.5: 6.0, and bis(trifluoroacetoxy) iodobenzene (323.0mg, 0.75mmol) and 1,2-dichloro Ethane (3.0mL), and trimethylsilylcyanide (75.0mg, 0.75mmol) was added under stirring, and anhydrous Na 2 SO 4 (36.0mg, 0.25mmol) and N, N-dimethylaniline A1 (61.0mg, 0.5mmol), after the addition is complete, continue stirring at this temperature for 1 hour to prepare N, N-dialkylaniline cyanide The reaction solution of compound B1.

[0035]...

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Abstract

The invention discloses a method for N, N-dialkylaniline cyanation reaction and belongs to the technical field of organic chemical synthesis. The method comprises the following steps: by taking benzene ring substituted N, N-dialkylaniline as a raw material, taking iodobenzene diacetate or di(trifluoroacetoxy) iodobenzene as an oxidant, taking trimethylsilyl cyanide as a cyaniding agent and taking anhydrous Na2SO4 as an additive, in the solvent, performing ice bath or performing one step reaction at room temperature, condensing and purifying to obtain the product. The method has the characteristics of simplicity, mild reaction condition, simplicity in operation, low production cost and convenience in popularization; the high-quality N, N-dialkylaniline cyanide product can be prepared by the method provided by the invention; the method can be widely used in the industrial production of the N, N-dialkylaniline cyanide; the product prepared by the method can be used for the synthesis of the bioactive compounds such as alpha-amino acid, 1, 2-diamine, tetrahydroquinoline, alpha-amino-aldehyde, ketone or beta-amino alcohol, and the wide demands of the market can be satisfied.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a method for cyanation reaction of N, N-dialkyl anilines. Background technique [0002] N, N-dialkylaniline cyanide is a very important organic synthesis intermediate, which is widely used in the construction of nitrogen-containing organic compounds, and is of great significance to the fields of medicine and material chemistry, such as α-amino acids prepared by hydrolysis under alkaline conditions , the reduced α-aminoaldehydes, ketones or β-aminoalcohols and asymmetric 1,2-diamines are pharmaceutical intermediates with important biological activities. In addition, they can be further converted into alkaloids such as tetrahydroquinoline and some other functional materials. Just because N, N-dialkylaniline cyanides are widely used in the synthesis of these compounds with biological activities and functions, they have broad market application prospec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B43/08C07C255/24C07C253/00C07D207/16
Inventor 熊燕沈行李加强潘静黄若峰张晓慧
Owner CHONGQING UNIV
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