Preparation method of thiocatbamate

A technology of thiocarbamate and mercaptan, applied in the field of carbonylation reaction, can solve the problems of unreported application and few literature reports of ionic liquid application

Inactive Publication Date: 2010-12-22
JIANGSU FOOD SCI COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Ionic liquids have been successfully used as reaction media and catalysts in many organic synthesis reactions due to their advantages of promoting reaction speed, improving reaction selectivity, and realizing the greening of the reaction process. There are few application literature reports
In particular, the application of adding supported catalysts in the carbonylation of aromatic nitro compounds in ionic liquids has not been reported.

Method used

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  • Preparation method of thiocatbamate
  • Preparation method of thiocatbamate
  • Preparation method of thiocatbamate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Nitrobenzene and ethanethiol are added in the container with stirring in a mol ratio of 1: 1.1 (that is, add 10mmol nitrobenzene, 11mmol ethanethiol in the container), and then add catalyst Pd-Fe / TiO to the container 2 36 mg (the mass percentage of Pd loading in the catalyst is 0.5%, and the mass percentage of Fe loading is 0.3%), ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim]PF 6 ) 10mL, vacuumize the container after sealing, the vacuum degree is lower than 400Pa, pass into normal pressure CO and replace three times, (pass CO once every 10 minutes or so, then evacuate to make the vacuum degree lower than 400Pa, then pass CO. pass CO. Mainly to exclude oxygen, and other gases, to ensure the purity of the reaction), at 30 ° C, about 500 Pa, stirring the reaction for 4 hours.

[0037] After the reaction, it was extracted with ethyl acetate (ether can also be used) (5 mL×3). The obtained extract was washed with water (5mL×3), and washed with anhydrou...

Embodiment 18

[0039] The ionic liquid selects acetonitrile (that is, adds 10 mL of acetonitrile in the container), and the obtained thiocarbamate The yield of thiocarbamate based on the nitro compound was 94.3%. The rest are implemented as in Example 1.

[0040] Table 3 shows the raw materials used (referring to aromatic nitro compounds and thiols or thiophenols), reaction time, yield and melting point of the obtained thiocarbamate in Examples 2-17. The rest are implemented as in Example 1.

[0041] table 3

[0042]

[0043]

[0044] It can be seen from Table 3 that under the determined optimized reaction conditions, Pd-Fe / TiO in ionic liquid 2 Catalyzes the carbonylation of a series of aromatic nitro compounds with thiols or with thiophenols. in Pd-Fe / TiO 2 Under the action of thiols of different structures, [bmim]PF 6 The carbonylation reaction can be carried out smoothly in the medium, and most thiols can obtain the corresponding thiocarbamate in a yield of more than 90%, wh...

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Abstract

The invention discloses a preparation method of thiocatbamate, comprising the following steps: adding an aromatic nitro compound and thiol or thiophenol into a container with a stirring function based on the mol ratio of 1:0.8-1.2, adding a catalyst Pd-Fe / TiO2 and an ionic liquid in the container in terms of that 25-45mg of the catalyst and 5-15mL of the ionic liquid are added in the container when per 10mmol of the aromatic nitro compound is added in the container, sealing the container, vacuumizing, introducing CO for replacement for more than one time when the vacuum degree is lower than 400Pa, stirring to react for 3-8h on the conditions that the temperature is 20-40 DEG C and the pressure is 400-1400Pa, extracting by an organic solvent after the reaction is finished to obtain extract, cleaning by water, drying, decompressing and evaporating the organic solvent to obtain a crude product, and performing recrystallization on the crude product by petroleum benzine to obtain the thiocatbamate.

Description

technical field [0001] The invention relates to the field of preparation of organic compounds, in particular to the preparation of aromatic nitro compounds and thiols or thiophenols in ionic liquids with Pd-Fe / TiO 2 For the carbonylation of catalysts, a method for preparing carbamates. Background technique [0002] Thiocarbamate is a compound containing oxygen, nitrogen, sulfur and other heteroatoms and various functional groups in the molecule. Most of them have good biological activity and are widely used in medicine, pesticides and organic synthesis. It can be used as herbicides, insecticides, fungicides, antiviral agents and biological regulators, etc. Therefore, it is of great significance to study the synthesis of these compounds. [0003] The methods reported in the literature for the synthesis of thiocarbamate mainly include hydrolysis and alcoholysis, isocyanate method, trichloroacetyl chloride method and carbonylation method. Carbonylation is a very effective non...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C333/08B01J23/89
Inventor 金德宽刘长春
Owner JIANGSU FOOD SCI COLLEGE
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