Preparation method for substituted diphenyl sulfide

A technology of diphenyl sulfide and chlorinated alkanes, which is applied in the field of preparation of substituted diphenyl sulfide, can solve the problems of high cost, complex reaction process, complex reaction process, etc., and achieve mild and stable synthesis reaction, high conversion rate of raw materials, Good product selection

Inactive Publication Date: 2010-07-14
QINGDAO UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The disadvantage of this method is that the iodobenzene compound is used as the raw material, which is expensive, the reaction process is complicated, and it is difficult to synthesize the target product with high yield under conventional

Method used

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  • Preparation method for substituted diphenyl sulfide
  • Preparation method for substituted diphenyl sulfide
  • Preparation method for substituted diphenyl sulfide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1: the synthesis of 4-fluorodiphenyl sulfide

[0016] Add diphenyl disulfide (88g, 0.4mol) and 300mL tetrachloride carbon, turn on the magnetic stirring, and slowly pass in the chlorine gas dried by concentrated sulfuric acid for 3 hours after it is completely dissolved; during this process, keep the internal temperature of the reaction solution not exceeding 20°C with a water bath, and then keep stirring at this temperature for 2 hours to stop the reaction; normal pressure Distill carbon tetrachloride and vacuum distillation to obtain 51g of red benzenesulfenyl chloride with a boiling point of 40-49°C / 2mmHg, with a yield of 88%. Aluminum (16g, 0.12mol), start stirring, and keep the temperature in the bottle in a water bath at 25°C, then add the prepared benzenesulfenyl chloride (11.3g, 0.1mol) dropwise for 1 hour; Continue to stir for 2 hours to complete the reaction; then slowly pour the reaction mixture into a stirred 200g ice-water mixture, separate laye...

Embodiment 2

[0017] Embodiment 2: the synthesis of 4-chlorodiphenyl sulfide

[0018] First synthesize 4-chlorobenzenesulfenyl chloride according to the corresponding steps and methods in Example 1; then add 100mL benzene and 100mL carbon tetrachloride, anhydrous aluminum trichloride (16g, 0.12mol) in a 500mL flask, and start stirring , the water bath kept the temperature in the bottle at 25°C, then added dropwise the prepared 4-chlorobenzenesulfenyl chloride (18g, 0.1mol) for 2 hours; after the dropwise addition, continued to stir for 2 hours at a temperature of 25°C to complete the reaction; then Slowly pour the reaction mixture into a stirred 200g mixture of ice and water, separate layers, and dry over anhydrous magnesium sulfate; finally remove carbon tetrachloride and unreacted benzene by vacuum distillation and collect The distillate obtained 19.5 g of colorless liquid with a yield of 74%, which was 4-chlorodiphenyl sulfide product; 1 HNMR (400M, CDCl 3 , TMS): δ=7.03 (ddt, J=8.8Hz,...

Embodiment 3

[0019] Embodiment 3: the synthesis of 4-chloro-4'-methyl diphenyl sulfide

[0020] First synthesize 4-chlorobenzenesulfenyl chloride according to the corresponding steps and methods in Example 1; then add 100mL toluene and 100mL dichloroethane, anhydrous zinc chloride (16g, 0.12mol) in a 500mL flask, start stirring, The water bath kept the temperature in the bottle at 25°C, and then added dropwise the prepared 4-chlorobenzenesulfenyl chloride (18g, 0.1mol) for 2 hours; after the dropwise addition, continued to stir for 2 hours at a temperature of 25°C to complete the reaction; then put The reaction mixture was slowly poured into a stirred 200g mixture of ice and water, separated into layers, and dried over anhydrous magnesium sulfate; finally, carbon tetrachloride and unreacted toluene were removed by atmospheric distillation, and the fraction with a boiling point of 183-185°C / 266Pa was collected by vacuum distillation Obtained 16.7 g of colorless liquid with a yield of 71%, n...

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Abstract

The invention relates to a synthesis method for organic compound, in particular to a preparation method for substituted diphenyl sulfide, belonging to the technical field of organic chemical substance preparation. Under the existence of Lewis acid catalyst, reaction temperature is controlled to be negative 10 DEG C to 70 DEG C to enable substituted benzene sulfenyl chloride and substituted benzene to take place Friedel-Crafts reaction in chloralkane solvent to generate substituted diphenyl sulfide. The used chloralkane solvent is mixed solvent formed by one or more of monochloromethane, dichloromethane, chloroform, carbon tetrachloride, dichloroethane and tetrachloroethane. The used catalyst is mixed catalyst formed by one or more of anhydrous ferric chloride, anhydrous aluminum chloride, titanium tetrachloride and anhydrous boron trifluoride. The invention has the advantages that the price of the raw materials is low, the synthesis reaction is mild and stable, the conversion rate of the raw materials is high, the product selectivity is good, the product can be easily separated from solvent, the product yield is high and the like.

Description

Technical field: [0001] The invention belongs to the technical field of preparation of organic chemical substances, and relates to a new synthesis method of organic compound substances, in particular to a preparation method of substituted diphenyl sulfide. Background technique: [0002] As we all know, aromatic sulfides, especially substituted diphenyl sulfides, are a class of organic compounds with pharmaceutical activity, which are widely used as drug intermediates in various therapeutic fields, such as diabetes, anti-infective drugs, immunity, Alzheimer's disease and Parkinson's Diseases, etc., especially in the field of modern pharmaceutical preparation technology, replacing diphenyl sulfide has more extensive development and application prospects. At present, many scholars and units at home and abroad have carried out research and experiments in this area, especially a lot of research and development on the preparation or synthesis of substituted diphenyl sulfides; U.S...

Claims

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Application Information

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IPC IPC(8): C07C319/14C07C323/09
Inventor 冯柏成于法暖刘鹏井丽倩
Owner QINGDAO UNIV OF SCI & TECH
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