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Method for synthesizing thioamide compound from 1,2,3-thiodiazole compound and amine under catalysis of copper

A technology for synthesizing thioamides and compounds, which is applied in the fields of organic chemistry, chemical instruments and methods, organic chemistry, etc., can solve problems such as incompatibility with arylamines, etc., and achieves cheap catalysts, high yields, and wide substrate adaptability. Effect

Active Publication Date: 2021-05-11
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The method of the invention has the advantages of low price, safe and simple operation, wide substrate applicability, high atom economy, and environmental friendliness, and solves the technical problem that the alkylamine used in the solvent amount in the existing method cannot be compatible with the arylamine

Method used

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  • Method for synthesizing thioamide compound from 1,2,3-thiodiazole compound and amine under catalysis of copper
  • Method for synthesizing thioamide compound from 1,2,3-thiodiazole compound and amine under catalysis of copper
  • Method for synthesizing thioamide compound from 1,2,3-thiodiazole compound and amine under catalysis of copper

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Under nitrogen protection, 0.05 mmol of copper acetate, 0.05 mmol of 4,5-bisdiphenylphosphine-9,9-dimethylxanthene, 0.5 mmol of 4-phenyl-1 , 2,3-thiodiazole, 0.5 mmoles of aniline and 3 ml of N,N-dimethylformamide were stirred and reacted at 90°C for 24h, the heating and stirring were stopped, and cooled to room temperature. Wash the reaction solution with saturated brine, extract with ethyl acetate, combine the organic phases, dry over anhydrous magnesium sulfate, filter, distill under reduced pressure to remove the solvent, and then separate and purify by column chromatography to obtain the target product. The eluent was a petroleum ether:ethyl acetate mixed solvent with a volume ratio of 10:1, and the yield was 90%.

[0047] The structural characterization data of the resulting product are as follows:

[0048] 1 H NMR (500MHz, CDCl 3 )δ=8.57(s,1H),7.54(d,J=7.9Hz,2H),7.46–7.38(m,2H),7.34(dd,J=13.0,6.4Hz,5H),7.22(t,J =7.4Hz, 1H), 4.25(s, 2H). The hydrogen spectrum ...

Embodiment 2

[0053] Under nitrogen protection, 0.05 mmol of copper acetate, 0.05 mmol of 4,5-bisdiphenylphosphine-9,9-dimethylxanthene, 0.5 mmol of 4-phenyl-1 , 2,3-thiodiazole, 0.5 mmoles of 2-methoxyaniline and 3 ml of N,N-dimethylformamide were stirred and reacted at 90°C for 24h, the heating and stirring were stopped, and cooled to room temperature. Wash the reaction solution with saturated brine, extract with ethyl acetate, combine the organic phases, dry over anhydrous magnesium sulfate, filter, distill under reduced pressure to remove the solvent, and then separate and purify by column chromatography to obtain the target product. The eluent was analyzed as petroleum ether with a volume ratio of 10:1: ethyl acetate mixed solvent, and the yield was 85%.

[0054] The structural characterization data of the resulting product are as follows:

[0055] 1 H NMR (500MHz, CDCl 3 )δ=9.16(s,1H),9.03(d,J=8.1Hz,1H),7.46–7.39(m,2H),7.36(t,J=6.9Hz,3H),7.12(t,J=7.8 Hz,1H),6.95(t,J=7.8Hz,1H),6.81...

Embodiment 3

[0060] Under nitrogen protection, 0.05 mmol of copper acetate, 0.05 mmol of 4,5-bisdiphenylphosphine-9,9-dimethylxanthene, 0.5 mmol of 4-phenyl-1 , 2,3-thiodiazole, 0.5 mmoles of 3-ethynylaniline and 3 ml of N,N-dimethylformamide were stirred and reacted at 90°C for 24h, the heating and stirring were stopped, and cooled to room temperature. Wash the reaction solution with saturated brine, extract with ethyl acetate, combine the organic phases, dry over anhydrous magnesium sulfate, filter, distill under reduced pressure to remove the solvent, and then separate and purify by column chromatography to obtain the target product. The eluent was analyzed as petroleum ether with a volume ratio of 10:1: ethyl acetate mixed solvent, and the yield was 92%.

[0061] The structural characterization data of the resulting product are as follows:

[0062] 1 H NMR (500MHz, CDCl 3 )δ=8.65(s,1H),7.59(d,J=10.4Hz,2H),7.39(t,J=7.0Hz,2H),7.33(t,J=8.0Hz,4H),7.25(t, J=7.7Hz,1H),4.20(s,2H),3.07(s,1...

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Abstract

The invention belongs to the technical field of organic chemistry, and discloses a method for synthesizing a thioamide compound from a 1,2,3-thiodiazole compound and amine under the catalysis of copper. The method comprises the following steps: in a protective atmosphere, taking an organic solvent as a reaction medium, reacting a 1,2,3-thiodiazole compound with an amine compound under the action of a copper salt catalyst or a copper catalyst and a phosphine ligand, and carrying out subsequent treatment to obtain the thioamide compound. According to the method, the copper salt is used as the catalyst, the phosphine ligand is adopted, the yield is high, and the substrate applicability is wide. In addition, the reaction takes the 1,2,3-thiodiazole compound and the amine compound as raw materials, and has the advantages that the raw materials are cheap and easy to prepare, the operation is simple and convenient, and the atom economy is high.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a copper-catalyzed method for synthesizing thioamide compounds from 1,2,3-thiodiazole compounds and amines. Background technique [0002] Not only is sulfur the fifth most common element in nature, but it is also essential to all forms of life. It exists in organisms in the form of organic sulfur compounds, such as three amino acids (cysteine, cystine and methionine), two vitamins (vitamin H and vitamin B1) and so on. Therefore, the research on organosulfides has always been one of the research hotspots in biochemistry and organic synthetic chemistry. In addition, organic sulfides occupy an important position in the field of organic superconductors, organic optoelectronic molecules and their devices due to their unique properties endowed by their special structures. [0003] As an important organic sulfide, thioamide only replaces the oxygen atom in the am...

Claims

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Application Information

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IPC IPC(8): C07B45/00C07C327/44C07D207/16C07D209/14C07D209/20C07D211/60C07D277/62C07D295/194C07D307/79C07D317/60
CPCC07B45/00C07C327/44C07D209/14C07D307/79C07D295/194C07D211/60C07D277/62C07D317/60C07D207/16C07D209/20C07C2602/08C07C2601/14
Inventor 黄良斌巫佳浩吕昌辉李小洪陈子廷
Owner SOUTH CHINA UNIV OF TECH
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