Method of synthesizing thiocarbamate by 'one pot method'

A technology for synthesizing thiocarbamate and carbamate, applied in organic chemistry, etc., can solve the problems of expensive catalyst, harsh reaction conditions, difficult post-processing, etc., and achieve great potential social and economic benefits, mild reaction conditions, Easy to store for easy access

Inactive Publication Date: 2006-06-14
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The above route mainly has the following disadvantages: 1) the raw materials are highly toxic or unstable; 2) the raw materials are not easy to get; 3) the catalyst used is expensive and difficult to recycle; 4) the synthesis process steps are various; Waste, Difficult to Reprocess
6) The reaction conditions are harsh and difficult to control

Method used

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  • Method of synthesizing thiocarbamate by 'one pot method'
  • Method of synthesizing thiocarbamate by 'one pot method'

Examples

Experimental program
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Effect test

Embodiment 1

[0016] The molar ratio of the feed material is substituted mercaptan: bis(trichloromethyl)carbonate: amine is 1.0:0.33:1.0, wherein the substituted mercaptan is p-cresol, the amine compound is aniline, and the organic solvent is methylene chloride , and its dosage is 15 times of the quality of p-cresol.

[0017] In a 150 mL four-neck flask equipped with a thermometer, a reflux condenser, and mechanical stirring, 40 mmol of p-cresylthiophenol, 13.3 mmol of bis(trichloromethyl)carbonate and 74.4 g of dichloromethane were added. Start stirring, dissolve, and react at room temperature for 1 hour. TLC traces until the reaction of the raw materials is complete. Cool the reaction solution to 0-5°C in an ice bath. Raise the temperature to reflux, stir for 2 h, cool to room temperature after the reaction, and wash the reaction solution with 10% NaHCO3, H2O, and saturated brine to obtain an aqueous phase and an organic phase, discard the aqueous phase, and dry the organic layer with an ...

Embodiment 2

[0019] The molar ratio of the feed material is substituted mercaptan: bis(trichloromethyl)carbonate: amine is 1.0:0.40:1.0, wherein the substituted mercaptan is p-cresol, the amine compound is aniline, and the organic solvent is methylene chloride , and its dosage is 15 times of the quality of p-cresol.

[0020] Others are with embodiment 1. The yield of the obtained thiocarbamate product is 78.8%, the melting point of the product is 129.0-130.0° C., and the purity is 98.5%.

Embodiment 3

[0022] The molar ratio of the feed material is substituted thiol: bis(trichloromethyl)carbonate: amine is 1.0:0.50:1.0, wherein the substituted mercaptan is p-cresol, the amine compound is aniline, and the organic solvent is methylene chloride , and its dosage is 20 times the mass of p-cresol.

[0023] Others are with embodiment 1. The yield of the obtained thiocarbamate product is 80.3%, the melting point of the product is 129.2-130.1° C., and the purity is 98.5%.

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Abstract

The present invention relates to a method for synthesizing thiocarbamate by using bis(trichloromethyl) carbonate, amines compound and substituted thioalcohol (including thiophenol compound) as raw material and adopting í‹one-pot methodíŒ reaction in organic solvent.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of thiocarbamate. (2) Background technology [0002] Before the present invention was made, the synthesis of thiocarbamate compounds in the prior art was mainly by the following route: 1) the reaction of phosgene, amine and mercaptan; 2) the reaction of carbamoyl chloride or isocyanate and mercaptan; 3) Intramolecular rearrangement reactions of various derivatives; 4) reactions of carbon monoxide, amines, and sulfur or disulfides in the presence of catalysts; 5) reactions of carbon monoxide, sulfur, amines, and halides; 6) trichloroacetyl chloride , the reaction of amine and thiol; 7) the reaction of thiocyanate and alcohol, etc. [0003] The above route mainly has the following disadvantages: 1) the raw materials are highly toxic or unstable; 2) the raw materials are not easy to obtain; 3) the catalyst used is expensive and difficult to recycle; 4) the synthesis process steps are numerous; Was...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C333/02
Inventor 苏为科张建萍
Owner ZHEJIANG UNIV OF TECH
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