Thioether compound and synthetic method and application thereof

A technology of disulfide compounds and compounds, applied in the formation/introduction of mercapto/thioether groups, thioether preparation, organic chemistry, etc., can solve the problems of easy pollution of the environment, harsh conditions, and not very mild reaction conditions, and achieve easy The effect of industrialized production, simple reaction equipment and simple conditions

Inactive Publication Date: 2018-11-09
GUANGDONG UNIV OF TECH
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  • Abstract
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  • Claims
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Problems solved by technology

[0003] But usually the synthesis of this type of thioether compound needs to use dichloromethane as a raw material at a relatively high temperature, and microwaves are also required to promote the reaction, which is easy to pollute the environment, and the reaction conditions are not very gentle (Can.J.Chem.84: 1529-1533 (2006))
Also catalyzed by expensive metal rhodium reagents, the reaction conditions are uneconomical (Appl.Organometal.Chem.2015,29,221–225)
Also use bromomethyllithium as a raw material to react to synthesize such thioether compounds. First of all, bromomethyllithium is difficult to prepare and needs to be prepared on-site, and this method needs to be carried out at -78 ° C, and the conditions are relatively harsh (Chem.Commun. ,2016,52,2639-2642)

Method used

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  • Thioether compound and synthetic method and application thereof
  • Thioether compound and synthetic method and application thereof
  • Thioether compound and synthetic method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1 2

[0036] The synthesis of embodiment 1 diphenylthiomethane

[0037] Take a 15mL pressure-resistant reaction tube, add 87mg (0.4mmol) of diphenyl disulfide, 260mg (0.8mmol) of cesium carbonate, 18-crown-6210mg (0.8mmol), 6mL of anhydrous acetone, and stir at 40°C for 24h . The mixture was stirred at 40°C for 24 hours under an air atmosphere. The reaction was quenched with saturated brine, extracted with ethyl acetate (EtOAc), washed with anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure. The residue was then purified by silica gel flash column chromatography with petroleum ether to obtain the desired product diphenylthiomethane 86 mg, yield 92%, as a white solid.

[0038] figure 1 It is the NMR H spectrum of diphenylthiomethane prepared in the present embodiment. figure 2 It is the NMR C spectrum of diphenylthiomethane prepared in the present embodiment. from figure 1 and 2 It can be seen from 1 H NMR (400MHz, CDCl3) δ7.43-7.41 (m, 4H), 7.31-7.29 (m, 4H), ...

Embodiment 2

[0043] Take a 15mL pressure-resistant reaction tube, add 87mg (0.4mmol) of diphenyl disulfide, 170mg (0.8mmol) of potassium phosphate, 18-crown-6210mg (0.8mmol), 6mL of anhydrous acetone, and stir at 40°C for 24h . The mixture was stirred at 40°C for 24 hours under an air atmosphere. The reaction was quenched with saturated brine, extracted with EtOAc, washed with anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure. The residue was then purified by silica gel flash column chromatography with petroleum ether to obtain the desired product diphenylthiomethane 51 mg, yield 54%, as a white solid.

Embodiment 3

[0045] Take a 15mL pressure-resistant reaction tube, add 87mg (0.4mmol) of diphenyl disulfide, 111mg (0.8mmol) of potassium carbonate, 18-crown-6210mg (0.8mmol), 6mL of anhydrous acetone, and stir at 100°C for 24h . The mixture was stirred at 100° C. for 8 hours under an air atmosphere. The reaction was quenched with saturated brine, extracted with EtOAc, washed with anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure. The residue was then purified by silica gel flash column chromatography with petroleum ether to obtain the desired product diphenylthiomethane 65.5 mg, yield 70%, as a white solid.

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Abstract

The invention belongs to the technical field of organic synthesis of sulfur-containing compounds and discloses a thioether compound and a synthetic method and application thereof. The thioether compound is prepared by the following steps: mixing acetone, a disulfide compound, inorganic base and 18-crown ether-6, heating and stirring, reacting under the action of a catalyst of inorganic base in theair atmosphere, concentrating and purifying to prepare the thioether compound. The molecular structural formula of the thioether compound is as shown in the formula (1) in the specification, whereinR1 and R2 are selected from hydrogen atom, alkyl group, alkoxy group, nitro group, amino group, hydroxyl group, halogeno, acyl group, aryl group or heterocyclic group. The use of high-toxicity halohydrocarbon, such as dichloromethane and diiodomethane is avoided by the method. The synthetic method has simple steps, is simple to operate and is feasible, is environmentally-friendly and has high conversion rate under mild conditions. Yield of the product reaches up to 96%. The thioether compound can be applied in the field of preparation of organic synthetic intermediates.

Description

technical field [0001] The invention belongs to the technical field of sulfur-containing organic synthesis, and more specifically relates to a thioether compound and its synthesis method and application. Background technique [0002] Due to the wide application of organosulfur compounds in biology, many drugs that can treat Parkinson's disease, cancer and malaria are sulfur-containing compounds (J.Med.Chem.2001,44,1202-1210), so it has attracted many focus on. And the thioether compound synthesized by this method is an important intermediate in organic synthesis (Synlett. 2013, 24, 1533-1540). [0003] But usually the synthesis of this type of thioether compound needs to use dichloromethane as a raw material at a relatively high temperature, and microwaves are also required to promote the reaction, which is easy to pollute the environment, and the reaction conditions are not very gentle (Can.J.Chem.84: 1529-1533 (2006)). In addition, it is catalyzed by expensive metal rho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B45/06C07C319/14C07C321/28C07C323/09C07C323/20C07D333/34
CPCC07B45/06C07C319/14C07C321/28C07C323/09C07C323/20C07D333/34
Inventor 王肖峰陈迁余国典温春晓黄昱霖区颖聪霍延平
Owner GUANGDONG UNIV OF TECH
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