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Preparation method of thioether compound

A technology of compound and mercapto compound, which is applied in the field of preparation of thioether compounds, can solve the problems of short reaction time, environmental pollution, and low cost, and achieve the effects of short reaction time, cheap raw materials, and easy operation

Active Publication Date: 2020-01-14
SICHUAN UNIVERSITY OF SCIENCE AND ENGINEERING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Aiming at the above-mentioned problems in the prior art, the present invention provides a method for preparing thioether compounds. The thioether compounds are prepared by olefin compounds and mercapto-containing compounds. The operation is simple, and the reagents used are easy to obtain and the cost is low. The time is short, effectively solving the problems of high cost, easy to cause environmental pollution and low yield

Method used

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  • Preparation method of thioether compound
  • Preparation method of thioether compound
  • Preparation method of thioether compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Add 20mg of styrene and 24mg of p-methylthiophenol into a clean and dry round bottom flask, then add 2mL of dichloromethane, slowly add 49mg of iodotrimethylsilane at room temperature, stir the reaction for no more than 15 minutes, and finally pass through the column Chromatographic separation afforded the product as a clear liquid. This liquid is carried out proton nuclear magnetic resonance spectrum, carbon spectrum analysis, is determined to be corresponding sulfide compound 1, and productive rate is 95%, its hydrogen nuclear magnetic resonance spectrum, carbon spectrum analysis results see respectively Figure 1~2 .

[0041] Depend on Figure 1~2 As can be seen, this thioether compound-test result is as follows: 1 H NMR (400MHz, CDCl 3 )δ7.40–7.31(m,4H),7.30–7.27(m,3H),7.11(m,2H),4.35(q,J=7.0Hz,1H),2.37(s,3H),1.69(d ,J=7.0Hz,3H). 13 C NMR (101MHz, CDCl 3 ) δ 143.41, 137.41, 133.26, 131.34, 129.54, 128.41, 127.37, 127.12, 48.44, 22.27, 21.21.

Embodiment 2

[0043] Add 36mg of m-bromostyrene and 29mg of p-methylthiophenol into a clean and dry round bottom flask, then add 2mL of toluene, slowly add 46mg of iodotrimethylsilane at room temperature, stir the reaction for no more than 15 minutes, and finally pass through the column Chromatographic separation afforded the product as a clear liquid. This liquid is carried out hydrogen nuclear magnetic resonance spectrum, carbon spectrum analysis, is determined to be corresponding sulfide compound two, and productive rate is 90%, its hydrogen nuclear magnetic resonance spectrum, carbon spectrum analysis results see respectively Figure 3-4 .

[0044] Depend on Figure 3-4 As can be seen, this thioether compound two test results are as follows: 1 H NMR (400MHz, CDCl 3 )δ7.44–7.42(m,1H),7.40–7.34(m,1H),7.24–7.19(m,3H),7.18–7.11(m,1H),7.12–7.03(m,2H).,4.23 (q,J=7.0Hz,1H),2.36(d,J=11.7Hz,3H),1.62(d,J=7.0Hz,3H). 13 C NMR (101MHz, CDCl 3 ) δ 145.84, 137.80, 133.52, 130.61, 130.41, 130.12,...

Embodiment 3

[0046] Add 36mg of p-bromostyrene and 29mg of p-methylthiophenol into a clean and dry round bottom flask, then add 2mL of dichloromethane, slowly add 24mg of trimethylchlorosilane at -10°C, and stir for no more than 15 minutes , and finally separated by column chromatography to obtain a transparent liquid product. This liquid is carried out H NMR spectrum, carbon spectrum analysis, is determined to be corresponding sulfide compound three, and yield rate is 93%, its H NMR spectrum, carbon spectrum analysis results see respectively Figure 5-6 .

[0047] Depend on Figure 5-6 As can be seen, the three test results of the thioether compounds are as follows: 1 H NMR (400MHz, CDCl 3 )δ7.45–7.37(m,2H),7.20(d,J=8.1Hz,2H),7.18–7.13(m,2H),7.07(d,J=8.0Hz,2H),4.25(q,J =7.0Hz, 1H), 2.34(s, 3H), 1.62(d, J=7.0Hz, 3H). 13 C NMR (101MHz, CDCl 3 ) δ 142.57, 137.70, 133.41, 131.41, 130.70, 129.59, 129.04, 120.73, 47.86, 22.05, 21.16.

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Abstract

The invention provides a thioether compound preparation method, which comprises: adding an olefin compound and a sulfydryl-containing compound to an organic solvent, adding a catalyst at a temperatureof -78 to 80 DEG C, stirring for 1-15 min, and purifying to obtain the thioether compound; wherein the molar ratio of the olefin compound to the sulfydryl-containing compound to the catalyst is 1: 1-1.5: 1-1.5; the molar volume ratio of the olefin compound to the organic solvent is 1: 8-12. According to the method, the thioether compound is prepared from the olefin compound and the sulfydryl-containing compound, the operation is simple, the used reagents are easy to obtain, the cost is low, the reaction time is short, and the problems that the cost is high, environmental pollution is easily caused and the yield is low are effectively solved.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a preparation method of thioether compounds. Background technique [0002] Thioether compounds are important synthons and catalysts or ligand skeletons, and they often appear in the materials, biology, and pharmaceutical industries. Among them, in the field of medicinal chemistry, thioether compounds usually have better activity. According to literature statistics, nearly 20% of the best-selling drugs in the United States belong to organic thioether compounds. Therefore, a large number of chemists are committed to finding efficient and convenient methods to synthesize such compounds and their derivatives. The commonly used preparation methods include: alkylation of thiols, coupling reactions of thiols and functionalization of thiols on alkenes reaction, etc., but the reagents used in these methods are relatively rare, which makes the cost higher, the alkyla...

Claims

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Application Information

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IPC IPC(8): C07C319/18C07C321/28C07C323/09C07C323/16C07D277/74
CPCC07C319/18C07D277/74C07C321/28C07C323/09C07C323/16
Inventor 梁鹏曾开耘曾羽周婷婷
Owner SICHUAN UNIVERSITY OF SCIENCE AND ENGINEERING