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Aryl alkyl thioether compounds and synthesis method thereof

A technology of aryl alkyl sulfide and synthesis method, which is applied to the formation/introduction of mercapto/thioether groups, chemical instruments and methods, preparation of thioether, etc., can solve problems that have not been reported, and achieve low price and low cost. The effects of wide applicability and simple ligand structure

Active Publication Date: 2014-05-14
EAST CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, no effective "drug molecule post-vulcanization" method has been reported

Method used

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  • Aryl alkyl thioether compounds and synthesis method thereof
  • Aryl alkyl thioether compounds and synthesis method thereof
  • Aryl alkyl thioether compounds and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Synthesis of benzyl (4-methoxyphenyl) sulfide:

[0036]

[0037] In a reaction tube, add CuCl (0.02mmol, 2.0mg), substrate 1 (0.2mmol, 24.6mg), BnCl (1.0mmol, 116μL), Na 2 S 2 o 3 ·5H 2 O (1.0mmol, 248mg), tert-butyl nitrite (0.3mmol, 40μL), methanol / water (1mL / 1mL), the reaction system was stirred at room temperature for 10 hours, and the reaction progress was monitored. After the reaction was completed, ethyl acetate (10 mL) was added to the system at room temperature, dried over anhydrous magnesium sulfate, filtered, concentrated, and separated by column chromatography to obtain a transparent solid 2 (2.3 mg, 5%), R f =0.50(PE:EA=20:1); 1 H NMR (400MHz, CDCl 3 )δ7.34–7.15(m,7H),6.83(d,J=7.8Hz,2H),4.02(s,2H),3.81(s,3H); 13 C NMR (100MHz, CDCl 3 )δ159.12, 138.05, 134.02, 128.83, 128.30, 126.92, 125.95, 114.34, 55.23, 41.15; IR (film) 2961, 1494, 1453, 1266, 1119, 822, 697cm -1 .

Embodiment 2

[0039] Synthesis of benzyl (4-methoxyphenyl) sulfide:

[0040]

[0041] In the reaction tube, add CuSO 4 ·5H 2 O (0.02mmol, 5.1mg), Substrate 1 (0.2mmol, 24.6mg), BnCl (1.0mmol, 116μL), Na 2 S 2 o 3 (1.0mmol, 248mg), tert-butyl nitrite (0.3mmol, 40μL), methanol / water (1mL / 1mL), the reaction system was stirred at room temperature for 10 hours, and the reaction progress was monitored. After the reaction was completed, ethyl acetate (10 mL) was added to the system at room temperature, dried over anhydrous magnesium sulfate, filtered, concentrated, and separated by column chromatography to obtain a transparent solid 2 (4.1 mg, 9%).

Embodiment 3

[0043] Synthesis of benzyl (4-methoxyphenyl) sulfide:

[0044]

[0045] In the reaction tube, add Na 2 S 2 o 3 ·5H 2 O (1.0mmol, 248mg), BnCl (1.0mmol, 116μL), CuSO 4 ·5H 2 O (0.02mmol, 5.1mg), methanol / water (1mL / 1mL), the reaction system was stirred at 80°C for 2 hours; after that, the reaction system was cooled to 0°C, and substrate 1 (0.2mmol, 24.6mg) was added , tert-butyl nitrite (0.3mmol, 40μL), and the reaction system was stirred at room temperature to 10 hours. Monitor the progress of the reaction. After the reaction was completed, ethyl acetate (10 mL) was added to the system at room temperature, dried over anhydrous magnesium sulfate, filtered, concentrated, and separated by column chromatography to obtain the target product 2 (9.2 mg, 20%).

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Abstract

The invention discloses aryl alkyl thioether compounds and a synthesis method thereof. The synthesis method comprises the steps: in a reaction solvent, with an arylamine derivative and halogenated hydrocarbon as reaction raw materials, and Na2S2O3 as a vulcanization reagent, in the presence of a copper reagent catalyst, and reacting to obtain the aryl alkyl thioether compounds. According to the synthesis method disclosed by the invention, raw materials are easy to obtain and low in price, the reaction operation is simple, the reaction conditions are mild, the yield is higher, the tolerance of a functional group is excellent, later-phase modification of compounds of medicines, sugars, amino acids and the like is successfully realized, and an efficient method for constructing a carbon-sulfur bond is provided for researches of medicinal chemistry and biology orthogonal chemistry.

Description

technical field [0001] The invention belongs to the technical field of organic compound technology application, and specifically relates to a class of aryl alkyl sulfide compounds and a synthesis method thereof. Background technique [0002] Aryl alkyl sulfide compound is a very important compound, which widely exists in various types of drugs shown below, including drug molecules, materials and foods containing thioether structure. Therefore, from some simple structures, commercially available in large quantities It is particularly important to construct C-S bonds on the obtained compounds. [0003] [0004] The traditional method of synthesizing aryl alkyl sulfide compounds is mainly through the preparation of thiol or thiophenol compounds. In this type of method, the organic sulfur used is easily oxidized and has a toxic effect on metal catalysts; the raw materials have a strong taste and are harmful to the environment and human body to varying degrees; the raw materi...

Claims

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Application Information

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IPC IPC(8): C07B45/06C07C323/62C07C323/63C07C323/54C07C321/28C07C323/09C07C323/20C07C323/48C07C323/67C07C319/14C07D213/70C07D209/08C07D307/88C07D261/16C07D239/69C07D401/04C07H15/18C07H1/00
Inventor 姜雪峰李一鸣
Owner EAST CHINA NORMAL UNIVERSITY
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