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Fluorine-containing thiocarbamate compound and synthesizing method thereof

A technology for fluorine-containing thiocarbamate and ester compounds, applied in the direction of organic chemistry and the like, can solve the problems of few reports on the synthesis of thiothiocarbamate, achieve good industrial application prospects, high selectivity and yield Effect

Inactive Publication Date: 2019-01-25
HUBEI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it has been found through research that so far there are fewer reports on the synthesis of monothiothiocarbamate

Method used

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  • Fluorine-containing thiocarbamate compound and synthesizing method thereof
  • Fluorine-containing thiocarbamate compound and synthesizing method thereof
  • Fluorine-containing thiocarbamate compound and synthesizing method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of O-(1,1,1,3,3,3-hexafluoropropan-2-yl)(3-oxopentan-2-yl)(phenyl)carbamate

[0031] Add 1.0 mmol of 3-oxopentan-2-yl 4-methylbenzenesulfonate, 1.2 mmol of phenylthioisocyanate, 1.5 mmol of triethylamine, and then 2 mL of hexafluoroisopropyl to the reaction vessel Alcohol, reacted at room temperature, after the reaction, washed with aqueous solution, then extracted with an organic solvent, dried, concentrated under reduced pressure to remove the solvent, and the crude product was separated by column chromatography to obtain the target product with a yield of 89%.

Embodiment 2

[0033] Synthesis of O-(1,1,1,3,3,3-hexafluoropropan-2-yl)(5-oxonan-4-yl)(phenyl)carbamate

[0034] Add 1.0 mmol of 5-oxononan-4-yl 4-methylbenzenesulfonate, 1.2 mmol of phenylthioisocyanate, 1.5 mmol of triethylamine, and then 2 mL of hexafluoroisopropyl to the reaction vessel Alcohol, reacted at room temperature, after the reaction, washed with aqueous solution, then extracted with an organic solvent, dried, concentrated under reduced pressure to remove the solvent, and the crude product was separated by column chromatography to obtain the target product with a yield of 85%.

Embodiment 3

[0036] Synthesis of O-(1,1,1,3,3,3-hexafluoropropan-2-yl)(6-oxoundecan-5-yl)(phenyl)carbamate

[0037]Add 1.0 mmol of 6-oxoundecane-5-yl 4-methylbenzenesulfonate, 1.2 mmol of phenylthioisocyanate, 1.5 mmol of triethylamine, and then 2 mL of hexafluoroisocyanate into the reaction vessel Propanol was reacted at room temperature. After the reaction, it was washed with aqueous solution, then extracted with an organic solvent, dried, evaporated and concentrated under reduced pressure to remove the solvent, and the crude product was separated by column chromatography to obtain the target product with a yield of 88%.

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Abstract

The invention provides a fluorine-containing thiocarbamate compound and a synthesizing method thereof, and belongs to the technical field of compound synthesis. The fluorine-containing thiocarbamate derivative is prepared from multiple components through a one-pot method. A chemical equivalent amount of alkali is added into a container which contains alpha-OTs substituted ketone, a substituted thiocyanate compound and a fluorine-containing alcohol compound to be stirred at the reaction temperature of 25-100 DEG C, washing is conducted with water or a saturated salt solution after reaction ends, extracting is conducted through an organic solvent, drying, depressurizing, distilling, concentrating and solvent removing are conducted, a coarse product is separated through column chromatography,and then the fluorine-containing thiocarbamate derivative is obtained. The method has the advantages that no transition metal catalysts exist, the raw materials are low in price and easy to obtain, an oligomer is wide in applicability, the reaction conditions are mild, the location selectivity is high, the yield is high, and the compound is environmentally friendly.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and relates to a fluorine-containing thiocarbamate compound and a synthesis method thereof. Background technique [0002] Thiocarbamate derivatives are a class of widely used compounds with good physiological and biological activities, and can also be used as vulcanizing agents and photoinitiators. The commonly used synthesis method of this type of compound is: under strongly alkaline conditions, primary or secondary amines react with carbon disulfide to generate corresponding aminodithioformates, and then react with halogenated alkyls to generate aminodithioformates, but Due to the need to react under strong alkaline conditions, the reaction substrate cannot contain alkali-sensitive groups, and there are disadvantages such as intermediates need to be separated and the reaction time is long. [0003] In recent years, in the literature reports on the synthesis of dithiocarbamat...

Claims

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Application Information

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IPC IPC(8): C07C333/08C07C333/06C07D213/75
CPCC07C333/06C07C333/08C07C2601/14C07D213/75
Inventor 汪钢强孙绍发郭海兵王航赵森石洋汪舰
Owner HUBEI UNIV OF SCI & TECH
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