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Environment-friendly preparation method of Z-3-thiocyanate thioacrylate compound

A technology of ester-based thioacrylate, Z-3-, applied in the field of organic intermediate synthesis, can solve the problems of limited practical application, no commercial products, complicated separation process, etc., achieves quantitative raw material conversion rate, low price, The effect of high catalytic activity

Inactive Publication Date: 2019-06-21
HUNAN UNIV OF SCI & ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, there is a deep eutectic solvent to catalyze the three-component reaction of thiopropiolate compound, potassium selenocyanate and water to obtain Z-3-selenocyanate group thioacrylate compound, such as (ACS SustainableChem .Eng.2019,7,2169-2175), but the reaction also has the following deficiencies, which limit its practical application:
[0003] 1) The deep eutectic solvent needs to be prepared, and there is no commercial product
[0004] 2) The productive rate of Z-3-selenocyanate group thioacrylate compound is 77~94%, there is E formula isomer and the decomposition product propiolic acid of thiopropiolate compound and unreacted The thiopropiolate compound raw material, the purity is not high
[0005] 3) The separation of the product needs to be extracted with a volatile organic solvent, and the purification of the product needs to be separated by silica gel column chromatography. The separation process is not only complicated and costly, but also causes environmental pollution

Method used

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  • Environment-friendly preparation method of Z-3-thiocyanate thioacrylate compound
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  • Environment-friendly preparation method of Z-3-thiocyanate thioacrylate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～3

[0050] Following examples 1~3 all react by following reaction equation:

[0051]

[0052] The specific operation steps are: in a 20mL reaction tube, sequentially add propyne thioacid methyl ester (10mmol), potassium selenocyanate (12mmol, 1.16g), water (10mmol, 0.18g), lactic acid (30mmol, 2.70g) , the resulting mixture was reacted in a 30W / 44KHz ultrasonic reaction device for 30 minutes. After the reaction, 13.5ml of water and lactic acid were added to form an aqueous lactic acid solution. Z-3-selenocyanatopropenylthioate was insoluble in the aqueous lactic acid solution and precipitated, separated, and vacuum-dried to calculate the weight.

Embodiment 1

[0054] raw material: Target product:

[0055] S-(p-tolyl)(Z)-3-selenocyanatoprop-2-enethioate:

[0056] Yield: 95%

[0057] 1 H NMR (400MHz, CDCl 3 )δ7.79(d, J=8.0Hz, 1H), 7.36(d, J=8.0Hz, 2H), 7.29(d, J=8.0Hz, 2H), 7.04(d, J=8.0Hz, 1H) ,2.41(s,3H).

[0058] 13 C NMR (100MHz, CDCl 3 )δ191.3, 140.9, 138.7, 134.3, 130.5, 124.7, 121.9, 105.7, 21.4.

[0059] HRMS Calcd(EI)m / z for C 11 h 9 NOSSe:[M] + 282.9570,found: 282.9574.

Embodiment 2

[0061] raw material: Target product:

[0062] S-phenyl(Z)-3-selenocyanatoprop-2-enethioate:

[0063] Yield: 94%

[0064] 1 H NMR (400MHz, CDCl 3 )δ7.53–7.52(m,2H),7.45–7.42(m,2H),7.38–7.37(m,1H),7.20(d,J=9.6Hz,1H),6.37(d,J=9.6Hz ,1H).

[0065] 13 C NMR (100MHz, CDCl 3 )δ186.1, 148.2, 134.6, 131.0, 129.4, 129.1, 128.4, 118.4.

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PUM

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Abstract

The invention discloses an environment-friendly preparation method of a Z-3-thiocyanate thioacrylate compound. The green preparation method comprises the following steps: under the action of ultrasonic waves, carrying out three-component addition reaction on a lactic acid catalytic thiopropiolate compound, thiocyanate and water to generate the Z-3-thiocyanate thioacrylate compound; after the reaction is ended, adding water into a system for diluting, thus separating out a high-purity Z-3-thiocyanate thioacrylate product. The method has the advantages of good product selectivity, high yield, simple separation process, low catalyst cost, environment friendliness and facilitation for industrial production and application.

Description

technical field [0001] The present invention relates to an environment-friendly preparation method of Z-3-selenocyanate-based thioacrylate compound, in particular to a method for catalyzing the one-step addition of thiopropiolate compound, selenocyanate and water by ultrasonic-assisted lactic acid The invention relates to a method for synthesizing Z-3-selenocyanate-based thioacrylate compounds, belonging to the technical field of organic intermediate synthesis. Background technique [0002] Z-3-selenocyanate-based thioacrylate compounds not only have very important physiological activities, but also contain selenocyanate functional groups, thioester groups, and alkene groups, which are all important modifiable functional groups. Important drugs and organic synthesis intermediate compounds. In the prior art, there is a deep eutectic solvent to catalyze the three-component reaction of thiopropiolate compound, potassium selenocyanate and water to obtain Z-3-selenocyanate group...

Claims

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Application Information

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IPC IPC(8): C07C391/00
Inventor 何卫民贾国凯陈红娟彭美陈兴华
Owner HUNAN UNIV OF SCI & ENG
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