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Alpha-ketothioamide compound and synthesis method thereof

A technology for ketone thioamides and amine compounds, applied in the field of α-ketothioamide compounds and their synthesis, can solve the problems of harsh conditions, generation of phosphorus waste, etc., and achieves low preparation cost, short reaction time, and substrates. wide range of effects

Pending Publication Date: 2019-11-29
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Lawesson's reagent is the traditional method for converting a carbonyl group to a thiocarbonyl group, but this sulfur-phosphorus reagent produces phosphorus waste
In addition, the Willger-Kindler reaction of aryl methyl ketones, amines and elemental sulfur can also be used to synthesize thioamides, but harsh conditions are required

Method used

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  • Alpha-ketothioamide compound and synthesis method thereof
  • Alpha-ketothioamide compound and synthesis method thereof
  • Alpha-ketothioamide compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Add 1mmol of α-azidoacetophenone, 3mmol of morpholine, 2mmol of elemental sulfur and 5ml of solvent THF into a 50mL round-bottomed flask, and react with magnetic stirring at room temperature for 3 hours. and saturated brine, left to stand to obtain an organic layer and an aqueous layer containing the product, after liquid separation, the organic layer was dried with anhydrous sodium sulfate, and the extraction solvent was evaporated under reduced pressure to obtain a crude product, which was washed with ethyl acetate / petroleum Ether = 1:15 (v / v) was used as the eluent for column separation and purification, and the eluent was evaporated under reduced pressure to obtain the yellow solid product 2-morpholino-1-phenyl-2-thioxoethanone with a yield of 94%. Such as figure 1 and figure 2 Shown, respectively, the obtained product 1 H NMR characterization spectrum and 13 C NMR characterization spectrum, the chemical shifts of the peaks corresponding to the product 2-morphol...

Embodiment 2

[0040] Add 1mmol of α-azidoacetophenone, 1.2mmol of morpholine, 1.5mmol of elemental sulfur and 5ml of solvent DMF into a 50mL round-bottomed flask, and react with magnetic stirring at room temperature for 0.5 hours. Ethyl ester and saturated brine were mixed, and the organic layer and water layer containing the product were obtained by standing still. After liquid separation, the organic layer was dried with anhydrous sodium sulfate, and the extraction solvent was evaporated under reduced pressure to obtain a crude product. The crude product was washed with ethyl acetate / Petroleum ether=1:20 (v / v) was used as the eluent for column separation and purification, and the eluent was evaporated under reduced pressure to obtain a yellow solid product 2-morpholino-1-phenyl-2-thioxoethanone with a yield of 86%.

Embodiment 3

[0042] Add 1mmol of α-azidoacetophenone and 5mmol of cyclopentylamine to a 50mL round bottom flask, add 4mmol of elemental sulfur and 5ml of solvent DMSO, and react with magnetic stirring at room temperature for 3 hours. Esters and saturated brine were mixed, and the organic layer and water layer containing the product were obtained by standing still. After liquid separation, the organic layer was dried with anhydrous magnesium sulfate, and the extraction solvent was evaporated under reduced pressure to obtain a crude product. The crude product was washed with ethyl acetate / Petroleum ether = 1:10 (v / v) was used as eluent for column separation and purification, and the eluent was evaporated under reduced pressure to obtain a yellow solid product N-cyclopentyl-2-oxo-2-(p-tolyl)sulfur On behalf of acetamide, the yield was 88%. Such as figure 1 and figure 2 Shown, respectively, the obtained product 1 H NMR characterization spectrum and 13 C NMR characterization collection, p...

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Abstract

The invention provides an alpha-ketothioamide compound and a synthesis method thereof. The alpha-ketothioamide compound is obtained by mixing an alpha-azidoacetophenone compound, an amine compound, elemental sulfur and a solvent, reacting for 0.5-4 hours to obtain a mixed solution, and separating and purifying. According to the method disclosed by the invention, the alpha-ketothioamide or the derivative thereof is obtained in a C-N bond breaking manner by taking the elemental sulfur as a sulfur source and the alpha-azidoacetophenone and the amine compound as substrates, so that the method is short in reaction time, simple in reaction system, mild in condition, environment-friendly, low in preparation cost and wide in substrate application range.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an α-ketothioamide compound and a synthesis method thereof. Background technique [0002] Thioamides are a class of organosulfur compounds, which contain a variety of derivatives and have a variety of physiological properties, such as anti-ulcer, anti-diabetes, anti-tuberculosis, anti-inflammatory, anti-tumor, antibacterial, agricultural herbicides, anti- Oxidizing agents, mold and yeast inhibitors. α-ketothioamides (α-ketothioamides), as one of the characteristic molecular fragments containing C=S double bonds, are useful intermediates for the synthesis of heterocyclic compounds, proteins, and drug molecules. [0003] So far, methods for the synthesis of α-ketothioamides have been reported. Lawesson's reagent is the traditional method for converting a carbonyl group to a thiocarbonyl group, but this sulfur-phosphorus reagent produces phosphorus waste. In...

Claims

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Application Information

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IPC IPC(8): C07D295/194C07C327/44
CPCC07D295/194C07C327/44C07C2601/08Y02P20/55
Inventor 陈云峰余佩
Owner WUHAN INSTITUTE OF TECHNOLOGY
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