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Synthesis method of dibenzyl sulfide

A technology of dibenzyl sulfide and synthesis method, applied in the field of synthesis of dibenzyl sulfide, capable of solving problems such as no literature reports

Active Publication Date: 2021-02-05
CHENGDU UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] To the best of our knowledge, there is no literature report identical to this application

Method used

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  • Synthesis method of dibenzyl sulfide
  • Synthesis method of dibenzyl sulfide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0009] Add N,N,N-trimethylbenzylammonium trifluoromethanesulfonate (2.4 mmol), sodium sulfide nonahydrate (1.0 mmol), acetonitrile into a dry 25 mL test tube with a stopper and a magnetic stirrer. (5.0 ml), and finally seal the ground test tube with a rubber stopper. The test tube was placed in an 85°C oil bath and stirred for 24 hours. The reaction mixture was then quenched by adding saturated sodium chloride solution (10 mL), extracted 3 times with ethyl acetate (15 mL), and the combined organic layers were washed with anhydrous MgSO 4 dried, and then adsorbed and dried with silica gel powder on a rotary evaporator. The silica gel powder adsorbed with the sample was transferred to a silica gel column, and purified by silica gel column chromatography (petroleum ether as eluent) to obtain a colorless oily liquid dibenzyl sulfide with a yield of 86%. The reaction equation is shown below.

[0010]

[0011] The structural characterization data of product dibenzyl sulfide ar...

Embodiment 2

[0014] N,N,N-trimethyl(4-methylbenzyl)ammonium trifluoromethanesulfonate replaces N,N,N-trimethylbenzylammonium trifluoromethanesulfonate in Example 1 to obtain colorless The yield of solid bis(4-methylbenzyl)sulfide was 80%.

[0015] 1H NMR (400MHz, CDCl3) δ7.27(d, J=8.0Hz, 4H), 7.21(d, J=8.0Hz, 4H), 3.65(s, 4H), 2.43(s, 6H).

Embodiment 3

[0017] N,N,N-trimethyl(3-methylbenzyl)ammonium trifluoromethanesulfonate replaces N,N,N-trimethylbenzylammonium trifluoromethanesulfonate in Example 1 to obtain light yellow The yield of oily liquid bis(3-methylbenzyl)sulfide was 80%.

[0018] 1H NMR (400MHz, CDCl3) δ7.20 (dd, J=44.4, 10.1Hz, 8H), 3.65(s, 4H), 2.41(s, 6H).

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Abstract

As an important organic intermediate and a synthesis reagent, an organic sulfur compound also has unique pharmacological effects of resisting tumors, inflammation, bacteria and oxidation, preventing aging, preventing and treating cardiovascular diseases and the like. The patent develops a method for synthesizing dibenzyl sulfide without metal catalysis. In an acetonitrile solution, benzyl trifluoromethanesulfonic acid quaternary ammonium salt and sodium sulfide nonahydrate are used to synthesize dibenzyl sulfide in a wide substrate range with good to excellent yield through breakage of a carbon-nitrogen bond and generation of a carbon-sulfur bond. The method has the advantages of mild reaction conditions, simple operation, no metal, high yield, wide substrate applicability and the like.

Description

technical field [0001] This patent relates to the research fields of organic synthesis, drug synthesis, and organic chemical industry. The specific method is to synthesize dibenzyl sulfide in the next step through the action of benzyltrifluoromethanesulfonate quaternary ammonium salt and sodium sulfide nonahydrate in acetonitrile. Background technique [0002] Thioethers have been used to build the main backbones of natural products, bioactive substances, and high-value materials, such as polymers for electronic materials and perfumes (- Procter, D.J.J. Chem. Soc., Perkin Trans. 1 2001, 335–354;( b) Procter, D. J. J. Chem. Soc., Perkin Trans. 1 2000, 835–871; (c) Block, E. Angew. Chem., Int. Ed. 1992, 31, 1135–1178.). Thioether (8.8%) is the third most typical component of sulfur-containing drugs, and it is also the most common scaffold material in sulfur-containing drugs. Representative drugs include cimetidine, thiethyl, perazine, pergolide, etc. (Ilardi E.A.; Vitaku, E.; ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/14C07C319/28C07C321/20C07C323/07C07C323/16
CPCC07C319/14C07C319/28C07C321/20C07C323/07C07C323/16
Inventor 曾庆乐唐琴琴
Owner CHENGDU UNIVERSITY OF TECHNOLOGY