Preparation method for synthesizing diaryl thioether compound based on L-cysteine

A technology of diaryl sulfide and cysteine, which is applied in the intermediate field of medicine and chemical industry, can solve the problems of inflammability and explosion, and achieve the effects of good compatibility, mild reaction conditions, great use value and social and economic benefits

Pending Publication Date: 2022-02-01
SHENYANG PHARMA UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most of the sulfur phenolic compounds have a bad smell, and the

Method used

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  • Preparation method for synthesizing diaryl thioether compound based on L-cysteine
  • Preparation method for synthesizing diaryl thioether compound based on L-cysteine
  • Preparation method for synthesizing diaryl thioether compound based on L-cysteine

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Experimental program
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Effect test

Embodiment 1

[0025] Example 1: Preparation of 4,4'-dimethyl diphenyl sulfide (1)

[0026] Put 109.0 mg (0.5 mmol) of 4-iodotoluene, 30.3 mg (0.25 mmol) of L-cysteine, 0.5 mmol of copper salt, 1.5 mmol of alkali, and 1.5 mL of solvent into a 15 mL reaction tube equipped with a magnet, Seal it with argon, heat and stir, and react for 12 hours. After the reaction, after the reaction solution was cooled to room temperature, the reaction solution was washed with 15 ml of water and transferred to a 250 ml separatory funnel, extracted three times with ethyl acetate, the organic layers were combined, the water layer was removed, and the ethyl acetate layer was washed with saturated salt After washing with water three times, it was dried by adding anhydrous magnesium sulfate. After rotary evaporation under reduced pressure and column chromatography (the mobile phase condition is petroleum ether), white crystals were obtained, which were the corresponding products shown in Formula 1. 1 H NMR (600M...

Embodiment 2

[0033] Embodiment 2: Preparation of 4,4'-diaminodiphenylsulfide (2)

[0034] 4-iodoaniline 109.5mg (0.5mmol) and L-cysteine ​​30.3mg (0.25mmol), cuprous iodide 95.2mg (0.5mmol), potassium hydroxide 84.2mg (1.5mmol), 1.5mL solvent DMSO / DMF=4:1 (v:v), placed in a 15mL reaction tube equipped with a magnet, sealed with argon, heated and stirred, and reacted in an oil bath at 120°C for 12 hours. After the reaction, after the reaction solution was cooled to room temperature, the reaction solution was washed with 15 ml of water and transferred to a 250 ml separatory funnel, extracted three times with dichloromethane, the organic layers were combined, the water layer was removed, and the ethyl acetate layer was washed with saturated salt After washing with water three times, it was dried by adding anhydrous magnesium sulfate. Rotary evaporation under reduced pressure and column chromatography (mobile phase conditions: petroleum ether / ethyl acetate = 10:1 (v / v)) obtained 30.9 mg of a...

Embodiment 3

[0037] Embodiment 3: Preparation of 3,3'-dimethyl diphenyl sulfide (3)

[0038] 3-iodotoluene 109.0mg (0.5mmol) and L-cysteine ​​30.3mg (0.25mmol), cuprous iodide 95.2mg (0.5mmol), potassium hydroxide 84.2mg (1.5mmol), 1.5mL solvent DMSO / DMF=4:1 (v:v), placed in a 15mL reaction tube equipped with a magnet, sealed with argon, heated and stirred, and reacted in an oil bath at 120°C for 12 hours. After the reaction, after the reaction solution was cooled to room temperature, the reaction solution was washed with 15 ml of water and transferred to a 250 ml separatory funnel, extracted three times with ethyl acetate, the organic layers were combined, the water layer was removed, and the ethyl acetate layer was washed with saturated salt After washing with water three times, it was dried by adding anhydrous magnesium sulfate. After rotary evaporation under reduced pressure and column chromatography (the mobile phase condition is petroleum ether), 41.4 mg of a yellow solid represent...

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Abstract

The invention belongs to the intermediate field of pharmaceutical chemical industry, and relates to a preparation method for synthesizing a diaryl thioether compound based on L-cysteine. The method comprises the following steps: under the protection of inert gas, adding substituted iodobenzene and L-cysteine into an aprotic polar solvent, then adding a copper salt catalyst and alkali, and reacting at 100-150 DEG C for 6-24 hours to obtain the diaryl thioether compound. The method has the advantages of simple and mild reaction conditions, safety, no toxicity, low price, simplicity and convenience in operation, good functional group compatibility, efficient reaction system, small environmental pollution and the like; diaryl thioether is an important pharmaceutical and chemical synthesis intermediate and chiral ligand, and has very wide application in the fields of biological medicine, organic synthesis, chemistry and chemical engineering and the like, so that the method has relatively high use value and social and economic benefits.

Description

technical field [0001] The invention belongs to the intermediate field of medicine and chemical industry, and relates to a preparation method for synthesizing diaryl sulfide compounds based on L-cysteine. Background technique [0002] Diaryl sulfide is the basic skeleton unit of many drug molecules. Diaryl sulfide compounds are widely used in the field of drug synthesis. These drugs can be used in the treatment of inflammation, diabetes, cancer, human immunodeficiency virus (HIV), schizophrenia disease, insomnia, high blood pressure, gastroesophageal reflux, Crohn's disease, Grave's disease, asthma, Alzheimer's disease, and Parkinson's disease. Diaryl sulfides are also precursors for the preparation of the corresponding sulfoxides and sulfones. In addition, diaryl sulfide compounds can also be used in the preparation of polymer materials, chemical dyes and pesticides. [0003] The classic method for the synthesis of diaryl sulfides involves the thermal reaction of arenes w...

Claims

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Application Information

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IPC IPC(8): C07C319/14C07C321/30C07C323/37C07C323/09C07C323/20C07C323/62
CPCC07C319/14C07C321/30C07C323/37C07C323/09C07C323/20C07C323/62
Inventor 肖琰许永男蒲香菱张辉
Owner SHENYANG PHARMA UNIVERSITY
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