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Synthesis method of benzyl sulfide

A technology of benzyl sulfide and synthetic method, applied in the directions of sulfide preparation, organic chemistry method, organic chemistry, etc., can solve problems such as no literature report

Active Publication Date: 2021-01-05
CHENGDU UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] As far as we know, there is no literature report similar to this application

Method used

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  • Synthesis method of benzyl sulfide
  • Synthesis method of benzyl sulfide
  • Synthesis method of benzyl sulfide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010]

[0011] Add 3-(toluene-4-sulfinyl)-propionic acid tert-butyl ester (1 mmol), N,N,N-trimethylbenzyl ammonium trifluoromethanesulfonate to a 25 mL clean glass test tube equipped with a stir bar (1.2mmol) and 5mL of acetonitrile were stirred at room temperature until the solid was completely dissolved and then 50% aqueous KOH (20mmol) was added. After the reaction was stirred for 24 hours in a preheated oil bath at 80 °C, the progress of the reaction was checked by TLC and the reaction was confirmed to be complete. The reaction mixture was cooled to room temperature. Then saturated sodium chloride solution (10 mL) was added to quench the reaction mixture, which was extracted three times with ethyl acetate (10 mL). The combined organic layers were washed with anhydrous MgSO 4 Dry, filter, and concentrate under reduced pressure. The residue was purified by flash column chromatography on silica gel (petroleum ether / ethyl acetate was used as eluent), and after purificat...

Embodiment 2

[0015] Use N,N,N-trimethyl(2-bromobenzyl)ammonium trifluoromethanesulfonate instead of N,N,N-trimethylbenzylammonium trifluoromethanesulfonate in Example 1 to obtain light yellow The yield of oily liquid (2-bromobenzyl)-p-tolyl sulfide was 87%.

[0016] 1 H NMR (400MHz, CDCl 3 )δ7.47(d,J=7.7Hz,1H),7.18–7.05(m,4H),7.04–6.96(m,3H),4.08(s,2H),2.23(s,3H).

Embodiment 3

[0018] Using N,N,N-trimethyl(4-tert-butylbenzyl)ammonium trifluoromethanesulfonate instead of N,N,N-trimethylbenzylammonium trifluoromethanesulfonate in Example 1, to obtain The yield of white solid (4-tert-butylbenzyl) p-tolyl sulfide is 85%

[0019] 1 H NMR (400MHz, CDCl 3 )δ7.18(dt,J=8.3,5.9Hz,6H),6.99(d,J=8.0Hz,2H),3.99(s,2H),2.23(s,3H),1.22(s,9H).

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Abstract

At present, there are many sulfur-containing drugs used for treating various diseases in the market, such as antipsychotic drug chloropropylthiophene; and sulfide has a wide biological activity, and not only can be easily converted into other types of sulfur-containing organic compounds, but also is an important intermediate for synthesis of many medicines. The invention discloses a metal-catalysis-free sulfide synthesis method which comprises the following steps: in an acetonitrile solution, benzyl trifluoromethanesulfonic acid quaternary ammonium salt and beta-sulfinyl ester are subjected tocarbon-nitrogen bond breakage and carbon-sulfur bond generation under the action of KOH, and the benzyl sulfide is synthesized in a wide substrate range at high yield to excellent yield. In the reaction in which the chiral quaternary ammonium salt participates, the chiral sulfide is reserved with a very good chiral value. The method has the advantages of mild reaction conditions, simple experimental operation, no metal catalyst, high product yield, wide substrate applicability, high chiral retention value and the like.

Description

technical field [0001] The patent involves the research fields of organic synthesis, drug synthesis, organic chemical industry, etc. The specific method is the transition metal-free one-step synthesis of benzyl sulfide compounds by β-sulfinyl ester and benzyltrifluoromethanesulfonic acid quaternary ammonium salt. . Background technique [0002] Currently, there are many sulfur-containing drugs on the market for the treatment of various diseases, such as the antipsychotic drug cloprothien (Luis E. Carmelo García, Virginie Lhiaubet-Vallet, Rolando Oyola1 and Miguel A. Miranda, Photochemistry and Photobiology, 2009, 85, 895–900.) and the antibacterial drug cefazolin (O.H. Jústiz, R. Fernández-Lafuente, J.M. Guisán, P. Negri, G . Pagani, M. Pregnolato, and M. Terreni, J. Org. Chem. 1997, 62, 9099-9106). Even more interesting is that thioethers have a wide range of biological activities. Not only is it easily converted into other types of sulfur-containing organic compounds, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/14C07C321/28C07C321/22C07C321/14C07C323/07C07C323/16C07C323/56C07C323/09C07C323/20C07D277/74C07D263/58C07D213/70
CPCC07C319/14C07D277/74C07D263/58C07D213/70C07B2200/07C07C2601/08C07C321/28C07C321/22C07C321/14C07C323/07C07C323/16C07C323/56C07C323/09C07C323/20
Inventor 曾庆乐张巧玲
Owner CHENGDU UNIVERSITY OF TECHNOLOGY