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Preparation method of diarylamine compound

A compound and aryl technology, which is applied in the field of preparation of diarylamine compounds, can solve problems such as toxicity, corrosion, and separation

Active Publication Date: 2019-04-12
盐城锦明药业有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of reaction conditions still has its application limitations, such as corrosion, toxicity, difficulty in catalyst handling, difficulty in separating from the reaction system, and generation of solid waste, etc.

Method used

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  • Preparation method of diarylamine compound
  • Preparation method of diarylamine compound
  • Preparation method of diarylamine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] In a 50ml reaction bottle, add 0.1g of copper oxide nanoparticles, 1g of chitosan and 20ml of toluene, sonicate to obtain a uniform suspension, and stir at room temperature to ensure that the chitosan surface adsorbs enough Cu2O nanoparticles, filter, Washed with ethanol and dried under vacuum at 50 °C to obtain CS-supported Cu 2 O(CS@Cu 2 O). Refer to this method to prepare CS@CuSO 4 , CS@CuI and CS@Cu(OAc) 2 to spare.

Embodiment 2

[0063]

[0064] Add bromobenzene, phenol, catalyst, alkali and solution to the reaction in sequence, heat and stir for 18 hours, add water to quench the reaction, filter, use for ethyl acetate extraction, wash with saturated brine, dry, concentrate, and perform silica gel column chromatography in diphenyl ether. To investigate the catalyst effectiveness of different reaction conditions, the specific data are as described in Table 1:

[0065] Table 1

[0066]

[0067]

[0068] a General reaction conditions: 1.5mmol phenol, 1.0mmol bromobenzene, 2.0mmol potassium phosphate, 1mL of anhydrous solvent; b3.0mmol potassium phosphate; c2mmol phenol.

[0069] Conclusion: Using the coupling reaction of bromobenzene and phenol as a template, the catalytic effects of different catalysts (A, B, C, D) were preliminarily evaluated. When 0.01 equivalent of [Cu] and 2 equivalents of K are present in DMF 3 PO 4 When , the coupling reaction of p-bromobenzene and phenol showed good p...

Embodiment 3

[0071]

[0072] Add 1mmol formula II-1 compound, 2mmol formula III compound, 0.5mmol% catalyst CS@Cu to the reaction successively 2 O. 3mmol potassium phosphate and 0.5ml N,N-dimethylformamide solution, heated to 110°C and stirred for reaction. After the reaction was detected by TLC, add water to quench the reaction, filter, use for ethyl acetate extraction, and wash with saturated saline , dried, concentrated, and the product was obtained by silica gel column chromatography.

[0073]

[0074]

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Abstract

The invention relates to a preparation method of a diarylamine compound. Specifically, under the catalysis of cuprous oxide supported by chitosan, the arylation reaction used for a nitrogen-containingheterocyclic compound is achieved, and the corresponding diarylamine compound is obtained. The preparation method of the diarylamine compound has the advantages that the process conditions are simple, the yield is good, the operability is strong, and the functional group tolerance is wide.

Description

technical field [0001] The invention belongs to the field of chemical industry and medicine, and relates to a preparation method of diarylamine compounds. Background technique [0002] N-arylazos are valuable compounds in the fields of organic synthesis, medicine or biology. One of the most common preparation methods is the Ullmann-type coupling reaction. In order to solve the problems of long reaction time, high temperature (>200°C) and the stoichiometric ratio of copper required for the catalyst, organic chemists screened different ligands to achieve aryl bromides and aryl bromides under mild conditions. Iodide coupling with phenol and imidazole. This type of reaction conditions still has its application limitations, such as corrosion, toxicity, difficulty in catalyst handling, difficulty in separating from the reaction system, and generation of solid waste. [0003] Immobilizing catalysts on heterogeneous supports is one of the main strategies to solve the above pro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/58C07D235/06C07D233/60C07D249/08C07D209/08B01J31/06B01J31/28B01J31/22C07C41/16C07C43/263
CPCC07C41/16C07D209/08C07D233/58C07D233/60C07D235/06C07D249/08B01J31/069B01J31/2239B01J31/28C07C43/263Y02A50/30
Inventor 钱存卫冯雪馨杨子健胡朝俊邱悦王庆东杨锦明
Owner 盐城锦明药业有限公司
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