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Method for catalysis synthesis of 1,3-diaminobenzene derivative by using cuprous dimethyl sulfide coordination compound

A technology of dimethyl sulfide and phenylenediamine, which is applied in the field of organic chemical synthesis and achieves the effects of high reaction selectivity, high total yield and easy purification

Inactive Publication Date: 2014-05-07
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, there is no relevant report on the catalytic synthesis of 1,3-phenylenediamine derivatives by cuprous dimethyl sulfide complexes

Method used

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  • Method for catalysis synthesis of 1,3-diaminobenzene derivative by using cuprous dimethyl sulfide coordination compound
  • Method for catalysis synthesis of 1,3-diaminobenzene derivative by using cuprous dimethyl sulfide coordination compound
  • Method for catalysis synthesis of 1,3-diaminobenzene derivative by using cuprous dimethyl sulfide coordination compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] A. Dissolve 10 g (93 mmol) of m-phenylenediamine in 20 ml of chloroform, and add dropwise to 30 ml of acetic anhydride under ice-cooling. Thereafter, the reaction was carried out at room temperature for 0.5 hour, and a large amount of white precipitates precipitated out. Suction filtration, washing with 20 ml of water three times, and drying gave 17.4 g of white solid (Compound 1), yield 98.4%.

[0022] B. 1 g (5.2 mmol) of compound 1, 1.65 g (15.6 mmol) of sodium carbonate, 125 mg (0.78 mmol) of CuClSMe 2 Add 20 ml of bromobenzene and react at 160°C for 8 hours. After the reaction was finished, bromobenzene was distilled off under reduced pressure, poured into 20 ml of acetone, heated to 55°C and filtered to remove insoluble matter. The acetone is spin-dried under reduced pressure to obtain a solid product, and the structural formula is

[0023]

[0024] 1 H NMR (400 MHz, CD 2 Cl 2 ), δ (ppm): 2.19 (s, 6H), 6.89 (s, 1H), 7.51 – 7.52 (d, J = 7.2 Hz, 2H), 7....

Embodiment 2

[0029] CuBrSMe for catalyst 2 , other with embodiment 1, obtains 1.220 gram target product. Yield 90.2%.

Embodiment 3

[0031] Alkali cesium carbonate, other with embodiment 1, obtains 1.241 gram target product. The yield is 91.7%.

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Abstract

The present invention provides a method for catalysis synthesis of a 1,3-diaminobenzene derivative by adopting a cuprous dimethyl sulfide coordination compound (CuX.SMe2) as a catalyst, wherein X is Br or Cl, and m-phenylene diamine is adopted as a raw material and is subjected to amidation, C-N bond coupling, hydrolysis and other reactions to prepare the target product. According to the present invention, the CuX.SMe2 catalyst has characteristics of high catalysis efficiency, product conversion rate increase, product selectivity increase and short reaction time, wherein the three-step reaction can be completed within a day; the total yield of the reaction is high, and can be more than 90%; the reaction selectivity is high, the obtained target compound has characteristics of high purity and easy purification, and the product with the purity of more than 98% can be obtained with the simple treatment; and the synthesis method is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a method for catalytically synthesizing 1,3-phenylenediamine derivatives with a cuprous dimethyl sulfide complex. Background technique [0002] Aromatic amine structural units are widely used in the construction of functional organic molecules: such as biologically active drugs, pesticides, fluorescent agents and electronic materials with photoelectric properties, etc. 1,3-Phenylenediamine derivatives are one of such widely used intermediates. It is a key intermediate in the synthesis of indolocarbazole anticancer drugs, and can also be used in the synthesis of free radical scavengers and high vitrification temperature of the hole transport material. [0003] Sheila I. et al have used Pd(dba) 2 As a catalyst to synthesize such compounds, the yield can reach 83%; Sebastien Kuhl et al. have also used nickel as a catalyst to synthesize such compounds, with a yie...

Claims

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Application Information

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IPC IPC(8): C07C211/55C07C211/51C07C209/62
Inventor 杨鹏刘程彬
Owner SHENYANG PHARMA UNIVERSITY