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Process for synthesizing thiocarbamate

A technology for synthesizing thiocarbamate and a new method, applied in the field of synthesizing thiocarbamate by catalytic reduction carbonylation reaction, can solve the problems of low atom economy, large amount of solvent, many operation steps, etc. The effect of high economy, stable product quality and simple raw materials

Inactive Publication Date: 2006-01-18
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has many steps, a large amount of solvent, and usually requires a large excess of one or two starting materials, low atom economy, and generally low yield, such as U.S. Patent US 3151119, US 3167571, US5565602

Method used

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  • Process for synthesizing thiocarbamate
  • Process for synthesizing thiocarbamate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] In a 100mL stainless steel autoclave, add nitrobenzene (10mmol), Se (0.5mmol), propanethiol (10mmol), Et 3 N (5mmol), after replacing three times with CO, raise the pressure of CO to 0.8MPa, put it into an oil bath that has risen to 50°C, stir and react for 10 hours, then cool to room temperature, open the kettle and deflate to obtain a solid crude product. Dissolve it in tetrahydrofuran, stir for 30 minutes, and filter to recover Se again. The filtrate was concentrated, purified by column chromatography, and the eluent was petroleum ether: chloroform (1:2), and the product was obtained by concentrating and removing the eluent. The product was propyl N-phenylthiocarbamate, and the yield was 83.5%. . It can also be directly recrystallized in petroleum ether to obtain colorless needle-like crystals.

Embodiment 2

[0022] The mercaptan is ethanethiol, and the consumption is 10 mmol. Other experimental methods and conditions are the same as in Example 1. The product is ethyl N-phenylthiocarbamate, and the actual yield is 80.0%.

Embodiment 3

[0024] The mercaptan is isopropyl thiol, and the consumption is 10 mmol. Other experimental methods and conditions are the same as in Example 1. The product is isopropyl N-phenylthiocarbamate, and the actual yield is 57.4%.

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Abstract

The synthesis process of thiocarbamate is one reaction process between mercaptan or thiophenol and aryl nitro compound in the presence of CO, Se as catalyst and triethylamine as co-catalyst in the condition with organic solvent or without solvent inside sealed high pressure reactor. The nitro benzene has substituent radical R1 in the benzene ring being H or one or several electron donating or electron drawing groups; and the sulfide has R2 capable of being alkyl group or one or several electron donating or electron drawing aryl groups. The molar ratio between mercaptan or thiophenol and aryl nitro compound is 0.1-10; the molar consumption of Se is 0.1-20 % of the reactant with less molar consumption; the molar consumption of triethylamine is 10-200 % of the reactant with less molar consumption; and the molar number of the organic solvent is 1-50 times that of the reactants. The reaction has period of 1-20 hr, temperature of 0-200 deg.c and CO pressure of 0.1-10 MPa.

Description

technical field [0001] The invention relates to thiocarbamate compounds, in particular to a method for synthesizing thiocarbamate by catalytic reduction carbonylation reaction. Background technique [0002] Thiocarbamate compounds are an important class of fine chemicals, which can be used as fungicides, insecticides and herbicides in pesticides; anesthetics, fungicides and antiviral agents in medicine. In addition, it is also an important intermediate of fine chemicals. [0003] At present, there are mainly three methods for synthesizing such compounds: one is the reaction of carbamoyl chloride with thiol or its derivatives. The raw material carbamoyl chloride used in this type of reaction is relatively complicated, the source is inconvenient, and the preparation method usually involves highly toxic phosgene, and a large number of by-products are generated in the reaction, so post-processing is difficult, such as US patents US 2913327, US 2983747, and US 3836524. The seco...

Claims

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Application Information

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IPC IPC(8): C07C333/08
Inventor 张晓鹏陆世维王树东
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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