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Method for synthesizing sulfoxide by oxidation of thioether

A technology for oxidizing sulfides and sulfoxides, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., to achieve high yield, mild reaction conditions, and environmental friendliness

Inactive Publication Date: 2013-06-05
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, only using hydrogen peroxide in the reaction system without adding catalysts and solvents will generally generate a large amount of excessive oxides

Method used

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  • Method for synthesizing sulfoxide by oxidation of thioether
  • Method for synthesizing sulfoxide by oxidation of thioether
  • Method for synthesizing sulfoxide by oxidation of thioether

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Experimental program
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Embodiment Construction

[0015] The structural formula of thioether of the present invention is , where R 1 and R 2 is C 1 ~C 4 Any one of the hydrocarbon groups, phenyl, p-nitrophenyl, p-methoxyphenyl, p-cyanophenyl, o-bromophenyl, p-bromophenyl, and R 1 and R 2 Not the same.

[0016] 1. Preparation of phenylmethyl sulfoxide:

[0017] 1. Oxidation reaction

[0018] Add 14.8 mg of magnesium nitrate, 48 mg of pyridinium tribromide, 2 ml of ethanol as a solvent, and 124 mg of sulfide anisole in a 10 ml round-bottomed flask. Stir the oxidation reaction in air at room temperature for 7 hours to obtain a crude product of phenylmethyl sulfoxide.

[0019] 2. Separation and purification

[0020] The crude phenylsulfoxide was quenched with saturated aqueous sodium thiosulfate solution, extracted with dichloromethane, and the organic phase was obtained and dried with anhydrous magnesium sulfate.

[0021] The product—benzyl sulfoxide was separated by column chromatography.

[0022] The data obtained f...

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Abstract

The invention relates to the technical field of chemical synthesis. In the method, thioether is oxidized in the air at room temperature so as to synthesize a crude sulfoxide compound on the basis of utilizing ethanol as a solvent and pyridine tribromide and nitrate as catalysts; or the thioether is oxidized in the air at room temperature so as to synthesize the crude sulfoxide compound on the basis of utilizing the ethanol as the solvent and liquid bromine and nitrate as the catalysts. The method is simple to operate and environment-friendly, and the product polluting environment is not generated by using the method, thereby overcoming the defects of thioether selective oxidation reaction; and the method has the characteristics of no transition metal catalyst, mild reaction conditions, less catalyst dosage, high oxidation selectivity, high yield and the like.

Description

technical field [0001] The invention relates to chemical synthesis technology, in particular to the technical field of sulfoxide synthesis. Background technique [0002] Sulfoxide compounds are chemically and biologically active organic intermediates that widely exist in biologically active drugs, such as antiulcer drugs, antibacterial drugs, antifungal drugs, anti-arteriosclerotic drugs, antihypertensive drugs, Cardiotonic agents, anti-vasodilators, etc. Due to the wide application of sulfoxide compounds in the fields of biology and medicine, more and more people are putting into the research of thioether oxidation reaction. [0003] Oxidation of thioethers is the most elegant method for the synthesis of sulfoxides. Many reagents can oxidize thioethers. Traditional oxidants include metal oxides, inorganic oxides, and organic oxides. However, most of these oxidants have low oxidation selectivity, which makes thioethers excessively oxidized to form sulfones, which increases...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C315/02C07C317/14C07C317/22C07C317/32
Inventor 袁宇刘伟石肖
Owner YANGZHOU UNIV