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New method for synthesis of alkenyl thiocyanate derivative

An alkenyl thiocyanate and derivative technology, applied in organic chemistry and other directions, can solve the problems of weak product configuration selectivity, poor functional group compatibility, poisoning of experimental operators, etc., and achieves good product configuration selectivity, Compatible and environmentally friendly effects

Active Publication Date: 2016-11-30
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The biggest problem with this type of method is that it is easy to pollute the environment during the production process, and has a certain poisonous effect on the experimental operator; in addition, the configuration selectivity of the product is not strong, and the poor compatibility of functional groups is also a practical problem
However, there is no report on the direct synthesis of alkenyl thiocyanate derivatives using alkyne halides as raw materials.

Method used

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  • New method for synthesis of alkenyl thiocyanate derivative
  • New method for synthesis of alkenyl thiocyanate derivative
  • New method for synthesis of alkenyl thiocyanate derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] In a 25ml reaction vessel equipped with a reflux condenser, add 0.2mmol of phenylacetylene bromide, 0.02mmol of silver acetate, 0.4mmol of potassium thiocyanate and 2ml of glacial acetic acid, stir and react at 100°C for 3 hours , stop heating and stirring, cool to room temperature, add aqueous sodium bicarbonate solution after filtration and extract three times with ethyl acetate, dry over magnesium sulfate, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The column chromatography eluent was petroleum ether:ethyl acetate mixed solvent with a volume ratio of 100:1, and the yield was 84%.

[0038] The structural characterization data of the resulting product are as follows:

[0039] IR(KBr):3065,2924,2854,2357,2120,735,692cm -1 .

[0040] 1 H NMR (400MHz, CDCl 3 ):δ7.49-7.43(m,5H),6.79(s,1H).

[0041] 13 C NMR (100MHz, CDCl 3 ): δ135.3, 134.4, 130.2, 128.9, 128.1, ...

Embodiment 2

[0045]In a 25ml reaction vessel equipped with a reflux condenser, add 0.2mmol of phenylacetylene bromide, 0.02mmol of silver chloride, 0.4mmol of potassium thiocyanate and 2ml of glacial acetic acid, and stir the reaction at 100°C for 3 hours After that, stop heating and stirring, cool to room temperature, add aqueous sodium bicarbonate solution after filtration and extract three times with ethyl acetate, dry over magnesium sulfate, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The eluent of the column chromatography was petroleum ether with a volume ratio of 100:1: ethyl acetate mixed solvent, and the yield was 56%.

Embodiment 3

[0047] In a 25ml reaction vessel equipped with a reflux condenser, add 0.2mmol of phenylacetylene bromide, 0.02mmol of silver bromide, 0.4mmol of potassium thiocyanate and 2ml of glacial acetic acid, and stir the reaction at 100°C for 3 hours After that, stop heating and stirring, cool to room temperature, add aqueous sodium bicarbonate solution after filtration and extract three times with ethyl acetate, dry over magnesium sulfate, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The column chromatography eluent is petroleum ether: ethyl acetate mixed solvent with a volume ratio of 100:1, and the yield is 53%.

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Abstract

Belonging to the technical field of pharmaceutical chemical synthesis, the invention discloses a method for synthesis of an alkenyl thiocyanate derivative. The method comprises the steps of: adding haloalkyne and thiocyanate as raw materials into a reaction vessel, taking a silver salt as the catalyst and using an organic solvent as the solvent, carrying out heating reaction, then cooling the obtained reacted solution to room temperature, and then performing purification, thus obtaining the alkenyl thiocyanate derivative. The method provided by the invention adopts haloalkyne and thiocyanate as the raw materials to carry out thiocyanation reaction for one-step synthesis of the alkenyl thiocyanate derivative. Use of concentrated sulfuric acid, mercury salt and other dangerous goods is avoided, the reaction raw materials are easily available, the reaction operation is safe and simple, the reaction process is environment-friendly, the substrate has wide applicability, the functional group has strong compatibility, the separation yield is high, the product configuration selectivity is good, the product can be enlarged to gram scale, and the product reserved halogen can be convenient for further conversion.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical chemical synthesis, in particular to a new method for synthesizing alkenyl thiocyanate derivatives. Background technique [0002] Thiocyanate compounds have a wide range of biomedical activities and are important structural units of many bioactive molecules and natural products. And studies have shown that thiocyanate compounds show excellent application potential in electrochemical reduction. In addition, thiocyanate compounds are important synthetic intermediates, which can be converted into sulfonic acid, sulfonyl chloride, thiocarbamate, thiol, sulfonyl nitrile and other compounds. For this reason, scientific researchers have conducted a lot of research on these compounds, and found that many thiocyanate compounds have strong inhibitory effects on parasites, bacteria and viruses. Although such compounds have such important applications, unfortunately there are few synthetic methods fo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C331/04C07C331/10C07D333/18
CPCC07C331/04C07C331/10C07D333/18
Inventor 江焕峰蒋光彬马志强伍婉卿
Owner SOUTH CHINA UNIV OF TECH
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