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A novel method for preparing a thioamide

A technology of thioamide and a new method, applied in the field of green catalytic synthesis, to achieve the effects of wide source of raw materials, simple experimental operation, reaction selectivity and high yield

Active Publication Date: 2017-11-21
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are no published documents and patent applications about iodine-catalyzed preparation of thioamides both at home and abroad.

Method used

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  • A novel method for preparing a thioamide
  • A novel method for preparing a thioamide
  • A novel method for preparing a thioamide

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0021] Add disulfide II (R=cyclohexane) into a 10mL reaction tube, add amines III (R 1 = pyridyl, R 2 =H) (1eq), elemental iodine (0.5eq), acetonitrile 1mL was added dropwise, and the reaction was carried out at 20°C for 5h. After the reaction, the target compound was separated by column chromatography to obtain a yellow solid with a yield of 97%.

preparation example 2

[0023] Add disulfide II (R=n-hexane) into a 10mL reaction tube, add amines III (R 1 = pyrimidinyl, R 2 =H) (1eq), elemental iodine (0.4eq), 1mL of tetrahydrofuran was added dropwise, and the reaction was carried out at 40°C for 8h. After the reaction, the target compound was separated by column chromatography to obtain a colorless liquid with a yield of 94%.

preparation example 3

[0025] Add disulfide II (R=neopentyl) into a 10mL reaction tube, add amines III (R 1 = furyl, R 2 =H) (1eq), elemental iodine (0.8eq), 1mL of dimethyl sulfoxide was added dropwise, and the reaction was carried out at 100°C for 5h. After the reaction, the target compound was separated by column chromatography to obtain a colorless liquid with a yield of 97%.

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Abstract

A thioamide preparing method is disclosed. According to the method, a nonmetal catalyst that is iodine is adopted as a catalyst, a disulfide and an amine compound are adopted as reaction substrates, and are effectively reacted at 20-140 DEG C in an organic solvent, and a thioamide compound can be efficiently, simply and conveniently prepared in 5-20 h. The method has advantages of a low cost, a high yield, simple and convenient operation, no pollution, and the like, and has certain feasibility for industrial production.

Description

【Technical field】 [0001] The invention belongs to the field of organic synthesis, and in particular relates to a green catalytic synthesis method using elemental iodine as a catalyst. In the method, aryl disulfide and aliphatic disulfide are used as substrates, various amines are used as raw materials, and the reaction can obtain the thioamide compound with higher yield in an organic solvent. 【Background technique】 [0002] Thioamides refer to a class of amides containing carbon-sulfur double bonds. Among the three atoms of the thioamide functional group, the carbon-sulfur double bond is used to improve the stability and catalytic activity of the target molecule. Thioamide compounds are very important organic compounds, not only used in the production of catalysts, stabilizers, pesticides, dyeing auxiliaries, mineral processing agents, etc., but also used in polymer vulcanizing agents, crosslinking agents, pharmaceutical raw materials and organic compound intermediates. W...

Claims

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Application Information

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IPC IPC(8): C07D213/75C07D239/42C07D307/66C07D265/30C07D241/04C07D207/14C07C327/42C07C327/48C07C327/46C07D213/83C07D239/28C07D307/68C07D207/16
CPCC07C327/42C07C327/46C07C327/48C07D207/14C07D207/16C07D213/75C07D213/83C07D239/28C07D239/42C07D241/04C07D265/30C07D307/66C07D307/68
Inventor 邱仁华李游许新华陈锦杨唐智
Owner HUNAN UNIV
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