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Thioamide analog compound synthesis method

A technology of thioamides and compounds, which is applied in the field of synthesis of thioamides, and can solve problems affecting the scope of application, complex catalyst preparation procedures, and difficulty in industrial production

Inactive Publication Date: 2006-07-26
朱凯琴
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

U.S. Patent US3700664 reports that acetonitrile synthesizes thioacetamide in the presence of a triethylamine catalyst, but the reaction needs to be carried out under high pressure, which is not easy for industrial production
Patent CN1102182 discloses an amine catalyst protruding on a polymer carrier to catalyze the addition reaction of acetonitrile and hydrogen sulfide, but the preparation process of the catalyst is complicated, which affects the application range of the process

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Thioacetamide

[0019] In a four-necked flask equipped with a stirrer, a thermometer, a reflux tube and a vent tube, add 82g of acetonitrile, 3.5g of sodium sulfide, 40ml of water and 4g of benzyltrimethylammonium chloride catalyst, and stir evenly. Steadily rise to 55°C, continuously feed hydrogen sulfide gas, and react for 2 hours. Then cool, filter, wash, and dry to obtain 138 g of a white solid product (92% yield); the melting point of the product is 111° C. to 114° C.

Embodiment 2

[0027] Thiopropionamide

[0028] Add 220g propionitrile, 900g toluene, 8g sodium sulfide, 100ml water and 5g methyl tridecyl ammonium chloride catalyst in a four-necked flask equipped with a stirrer, thermometer, reflux tube and vent tube, and stir evenly. Steadily rise to 70°C, continuously feed hydrogen sulfide gas, and react for 3 hours. Then cool, filter, wash, and dry to obtain 312 g of a yellow solid product (yield 87.6%); the melting point of the product is 41° C. to 43° C.

Embodiment 3

[0030] Thionicotinamide

[0031] In a four-necked flask equipped with a stirrer, a thermometer, a reflux tube and a vent tube, add 416g of pyridylcarbonitrile, 900g of chlorobenzene, 8g of sodium sulfide, 400ml of water and 10g of methyltriphenylphosphine bromide catalyst, and stir evenly . Steadily rise to 90°C, continuously feed hydrogen sulfide gas, and react for 3 hours. Then it was cooled, filtered, washed, and dried to obtain 492 g of a yellow solid product (89.1% yield); the melting point of the product was 184° C. to 190° C.

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Abstract

The invention discloses a synthesis of an addition reaction which uses accelerant to catalyze alkali and hydrogen sulfide in order to synthesize relevant thioamide compounds by high yield. The concrete things are thioacetamide, propanethioamide, thioisonicotinamide, thiobenzamide, 2-cyanothioacetamide, 4-chlorphenylthioacetamide, 4-methylthiobenzamide. The process of this invention is: dissolving nitrile in a suitable organic solvent, adding alkali solution and phase transfer catalyst, mixing adequately to homogeneous phase, then importing hydrogen sulfide until the reaction end and getting thioamide.

Description

technical field [0001] The present invention relates to the synthesis method of thioamide compound, specifically refers to thioacetamide, thiopropionamide, thionicotinamide, thiobenzamide, 2-cyanothioacetamide, 4-chlorophenyl Thioacetamide and 4-methylthiobenzamide. Background technique [0002] Thioamide compounds are a very important class of organic compounds, not only used in the production of catalysts, stabilizers, polymerization inhibitors, electroplating additives, photographic medicines, pesticides (such as fungicides, insecticides), dyeing auxiliaries, mineral processing agents etc. It can also be used as vulcanizing agent, crosslinking agent, rubber additives, and pharmaceutical raw materials for polymers, and it plays a huge role in petrochemical, nanomaterials, and organic synthesis. [0003] Thioamides are usually synthesized from the addition reaction of the corresponding nitriles with hydrogen sulfide: [0004] <chemistry num="001"> <chem file="2...

Claims

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Application Information

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IPC IPC(8): C07C327/38
Inventor 朱凯琴
Owner 朱凯琴
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