Method for preparing secondary aromatic amine or tertiary aromatic amine by conducting amination on aryl halide or alkyl halide

A technology for halogenated alkane amines and halogenated aromatic hydrocarbons is applied in the field of synthesizing aromatic secondary amines or tertiary amines, which can solve the problems of unsuitability for large-scale production, harsh atmosphere requirements and high reaction pressure, avoid side reactions that are difficult to control, realize industrialized production, The effect of mild reaction conditions

Inactive Publication Date: 2018-12-21
FUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reaction must be carried out under the condition of hydrogen, the reaction pressure is high, and the process requirements are high, so it is not suitable for large-scale production
[0006] In the above reports, the amination reaction temperature is high, the atmosphere is harsh, the cost is high, the preparation process is cumbersome, and the problems that need to be solved in the amination of organic compounds are virtually increased.

Method used

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  • Method for preparing secondary aromatic amine or tertiary aromatic amine by conducting amination on aryl halide or alkyl halide
  • Method for preparing secondary aromatic amine or tertiary aromatic amine by conducting amination on aryl halide or alkyl halide
  • Method for preparing secondary aromatic amine or tertiary aromatic amine by conducting amination on aryl halide or alkyl halide

Examples

Experimental program
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Effect test

Embodiment 1

[0030] 1. Purification of solvent and reaction substrate

[0031] Measure 100 milliliters of acetonitrile, and carry out vacuum distillation in a vacuum distillation device to remove impurities and water contained in the solvent, and then transfer it to N 2 Keep in the protective glove box. The reaction substrates chlorobenzene and aniline were transferred to the glove box in the same way as above for subsequent use.

[0032] 2. N 2 Configure the reaction system under the atmosphere

[0033] Add 5 milliliters of solvent acetonitrile obtained in step (1) into a quartz reactor equipped with a magnetic stirrer, then add 100 microliters of chlorobenzene and 100 microliters of aniline to the container successively, then seal the reactor and move out of the glove box .

[0034] 3. Reaction system pretreatment

[0035] Place the sealed quartz reactor with the reaction substrate in an ultrasonic machine for 30 minutes, and then place it on a magnetic stirrer with a stirring rate ...

Embodiment 2

[0039] The specific organic amine synthesis method is basically the same as in Example 1 of this part, except that chlorobenzene is changed to 4-methylchlorobenzene.

Embodiment 3

[0041] The specific organic amine synthesis method is basically the same as in Example 1 of this part, except that chlorobenzene is changed to 4-methoxychlorobenzene.

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Abstract

The invention discloses a method for preparing secondary aromatic amine or tertiary aromatic amine by conducting amination on aryl halide or alkyl halide. That is to say, the alkyl halide or the arylhalide and organic amine are mixed according to a certain ratio, and under light irradiation, C-N coupling reaction is carried out, so that a corresponding target product is generated for preparing the secondary amine or the tertiary amine. Compared with existing synthesis technologies, the method has the advantages that the aryl halide or the alkyl halide which is cheap and easy to get is selected as a reaction substrate, the method has good universality for different organic amine separately, moreover, the product selectivity is high, and separation and purification are easy; moreover, the synthesis method does not need to be conducted under severe conditions of high temperature and the like, a green and sustainable light source is adopted as driving force, the atom economy is high, andthe method has wide application prospects.

Description

technical field [0001] The invention relates to a method for synthesizing aromatic secondary or tertiary amines with halogenated aromatic hydrocarbons or halogenated alkanes and organic amines under light conditions. Background technique [0002] Aromatic amine compounds are commonly found in the synthesis of drugs, agricultural pesticides, dyes, pigments, rubber, etc., and are more widely used in bioactive substances and drugs. Therefore, the construction of C-N compounds has attracted the interest of many researchers. The traditional synthetic routes include nitration reduction method, Uimann synthesis method and SNAr synthesis method. However, these methods generally have problems such as poor applicability, cumbersome steps, poor selectivity, and harsh reaction conditions. The metal catalysts developed gradually in recent decades, including Pd, Co, Fe, Rh, Ru, Mn, Cu, Ag, Ir, etc., have been widely used in organic synthesis to catalyze the coupled amination reaction of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/55C07C209/10C07C233/07C07C231/08C07C233/65
CPCC07C209/10C07C231/08C07C211/55C07C233/65C07C233/07
Inventor 员汝胜王巍王乐乐魏英聪黄威超
Owner FUZHOU UNIV
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