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Method for synthesizing other amiprid from amiprid

A technology for the synthesis and compound of amidines, applied in the direction of organic chemistry, etc., can solve the problems of cumbersome product post-treatment, harsh reaction conditions, long reaction time, etc., and achieve the effect of simple product separation and purification, mild reaction conditions, and high product yield

Active Publication Date: 2018-09-14
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The method for synthesizing amidine by the above method has relatively harsh reaction conditions, generally requires higher temperature, and the reaction time is longer; due to the use of a large amount of water or air reagents, the post-treatment of the product is relatively cumbersome

Method used

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  • Method for synthesizing other amiprid from amiprid
  • Method for synthesizing other amiprid from amiprid
  • Method for synthesizing other amiprid from amiprid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The preparation of N-phenyl benzamidine, structural formula is as follows:

[0026]

[0027] Under nitrogen protection, the raw material N-methyl-N-phenylbenzamidine (0.5 mmol) and the catalyst Lu(CH 2 Ph) 3 (10mol%), aniline (1 mL), reacted at 60 °C for 12 h, and the isolated yield of the product was 91%.

[0028] 1 H NMR (400 MHz, CDCl3): δ 7.87-7.86 (m, 2H), 7.50-7.43 (m, 3H), 7.40-7.36 (m, 2H), 7.11-7.07 (m, 1H), 7.01-7.00 ( m, 2H), 4.93 (s, 2H).

Embodiment 2

[0030] The preparation of N-(2,6-dimethylphenyl) benzamidine, the structural formula is as follows:

[0031]

[0032] Under nitrogen protection, the raw material N-methyl-N-phenylbenzamidine (0.5 mmol) and the catalyst Lu(CH 2 Ph) 3 (10mol%), 2,6-dimethylaniline (1 mL), reacted at 60 °C for 12 h, and the isolated yield of the product was 83%.

[0033] 1 H NMR (400 MHz, CDCl3): δ 7.87-7.85 (m, 2H), 7.45-7.38 (m, 3H),7.05-7.03 (m, 2H), 6.90-6.87 (m, 1H), 4.60 (s, 2H), 2.13 (s, 6H).

Embodiment 3

[0035] The preparation of N-(2,6-dimethylphenyl)-4-methylbenzamidine, the structural formula is as follows:

[0036]

[0037] Under nitrogen protection, the raw material N-methyl-N-phenylbenzamidine (0.5 mmol) and the catalyst Lu(CH 2 Ph) 3 (10mol%), 4-methylaniline (1 mL), reacted at 60 °C for 12 h, and the isolated yield of the product was 76%.

[0038] 1 H NMR (400 MHz, CDCl3): δ 7.75-7.73 (m, 2H), 7.19-7.17 (m, 2H),7.03-7.01 (m, 2H), 6.89-6.85 (m, 1H), 4.57 (s, 2H), 2.37 (s, 3H), 2.11 (s, 6H).

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Abstract

The invention belongs to the technical field of chemical industry and particularly relates to a method for synthesizing other amiprids from an amiprid. Under a rare earth catalytic system, a amiprid and a primary amine or the primary amine generates a new amiprid through degradation and recombination reaction of the amiprid. The method for synthesizing other amiprids from an amiprid has the advantages of adopting a wide range of raw materials or the raw materials easy to prepare, having simple operation, being capable of synthesizing amiprid derivatives in high yield under mild conditions, andhaving high selectivity of reaction.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and in particular relates to a method for preparing other amidines from one amidine. Background technique [0002] Amidine derivatives are important intermediates in organic synthesis, and compounds with this skeleton widely exist in natural products and drug molecules. In addition, the compound is an important organic catalyst and super base, and also an important ligand in coordination chemistry. [0003] In the existing preparation technology, amidine compounds are usually prepared by reacting aromatic amines and nitriles under severe reaction conditions, such as high temperature, excessive use of strong Lewis acid, metal sodium or lithium, etc. for a long time. Literature (J. Chem. Soc., 1953, 6, 255-271 and Tetrahedron, 1981, 37, 2909-2910) reported that aromatic nitrile and amine were used as raw materials, and heated to 160- Preparation of amidine derivatives at 210°C; literatu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C257/18
CPCC07C257/18
Inventor 周锡庚张德兴
Owner FUDAN UNIV
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