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Process for synthesizing 2-(diphenyl methyl sulfinyl) acetamide

A technology of diphenylmethylsulfinyl and synthesis method, which is applied in the synthesis field of substituting acetamide, can solve the problems of large emissions and environmental pollution, and achieve the effects of accelerating the reaction process, shortening the reaction time, and increasing the product yield

Inactive Publication Date: 2007-06-20
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The process uses the corrosive agent thionyl chloride and the giant drug dimethyl sulfate, and needs to discharge a large amount of industrial waste water containing acid and alkali, which has great pollution to the environment

Method used

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  • Process for synthesizing 2-(diphenyl methyl sulfinyl) acetamide
  • Process for synthesizing 2-(diphenyl methyl sulfinyl) acetamide
  • Process for synthesizing 2-(diphenyl methyl sulfinyl) acetamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) Preparation of methyl diphenylmethyl thioacetate: Add benzhydryl mercaptan (2g, 10mmol), 1-butyl-3-imidazole tetrafluoroborate (4ml) successively in a 50ml round bottom flask, chlorine Methyl acetate (2.16g, 20mmol), put it in a microwave oven, and irradiate it with microwave (70W) for 3min, cool it down, extract the product with toluene (2×10ml), wash twice with water, dry, and concentrate to obtain an oily liquid 2.26 g, yield 83.1%, bp=370.1°C.

[0030] IR(KBr)v: 1736(C=O), 1600, 1493(Ar), 702(C-S)cm -1 .

[0031] MS (m / e): 272 (M + ), 258, 199, 167 (base peak), 152, 87, 72, 45.

[0032] (2) Preparation of methyl diphenylmethyl thioacetate: Add methyl diphenylmethyl thioacetate (2.72g, 10mmol) and hydrogen peroxide (4ml) successively in a 50ml round-bottomed flask, and put it in a microwave oven Radiation (70W) 5min, cooling. Then the product was extracted with dichloromethane (2×10ml), washed twice with water, dried and concentrated to obtain 1.9g of oily l...

Embodiment 2

[0040] (1) Preparation of isobutyl diphenylmethylthioacetate: Add benzhydryl mercaptan (2g, 10mmol), 1-butyl-3-imidazole tetrafluoroborate (4ml) successively in a 50ml round bottom flask, Isobutyl chloroacetate (3.02g, 20mmol), placed in a microwave oven with the open mouth exposed to microwave radiation (70W) for 3min, cooled, the product was extracted with toluene (2×10ml), washed twice with water, dried, and concentrated to obtain an oil Liquid 2.65g, yield 84.4%.

[0041] 1 H NMR (500MHz CDCl 3 )δ: 7.24, 7.45 (m, 10H, Ar), 5.42 (s, 1H), 3.88, 3.87 (d, 2H, CH 2 ), 2.41(d, 2H, CH 2 )2.06(m, H, CH), 0.93, 0.95(m, 6H, CH 3 ).

[0042](2) Preparation of isobutyl diphenylmethyl thioacetate: Add isobutyl diphenylmethyl thioacetate (3.14g, 10mmol) and hydrogen peroxide (4ml) successively in a 50ml round bottom flask, and put it in a microwave oven After microwave radiation (70W) for 5min, cool down. Then the product was extracted with dichloromethane (2×10ml), washed twice ...

Embodiment 3

[0049] (1) Preparation of isoamyl diphenylmethylthioacetate: Add benzhydryl mercaptan (2g, 10mmol), 1-butyl-3-imidazole tetrafluoroborate (4ml) successively in a 50ml round bottom flask, Isoamyl chloroacetate (3.3g, 20mmol), put it in a microwave oven, and irradiate it with microwave (70W) for 3min, then cool it, extract the product with toluene (2×10ml), wash twice with water, dry, concentrate to get an oil Liquid 2.74g, yield 83%.

[0050] (2) Preparation of isoamyl diphenylmethyl thioacetate: Add isoamyl diphenylmethyl thioacetate (3.28g, 10mmol) and hydrogen peroxide (4ml) successively in a 50ml round bottom flask, and put it in a microwave oven After microwave radiation (70W) for 5min, cool down. Then the product was extracted with dichloromethane (2×10ml), washed twice with water, dried and concentrated to obtain 2.46g of oily liquid with a yield of 75%.

[0051] (3) Preparation of benzhydryl sulfinylacetamide: in a 100ml three-necked round-bottomed flask equipped with...

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Abstract

The invention relates to a process for synthesizing 2-(diphenyl methyl sulfinyl) acetamide comprising the steps of, (1) at the presence of microwave radiation, reacting dibenzene methanethiol and chloroacetates in ionic liquids at 20-150 deg. C, separating to obtain compound of formula (I), (2) at the presence of microwave radiation, subjecting the compound of formula (I) to oxidizing reaction at 0-100 deg. C, separating to obtain compound of formula (II), (3) ammonolyzing the compound of formula (II) in ionic liquid at 0-100 deg. C, separating to obtain the said product.

Description

(1) Technical field [0001] The present invention relates to a synthetic method using a substituted acetamide. (2) Background technology [0002] Modafinil (Modafinil, CRL-40476, trade name Provigil), chemical name 2-(diphenylmethylsulfinyl) acetamide, is a new type of drug developed by French Lafon company that acts on the central nervous system. mind-boosting drugs. After 1994, it was successively launched in France, the United Kingdom, and Germany. It was approved to be launched in the United States in December 1998. It is mainly used for the treatment of narcolepsy and spontaneous hypersomnia. It is the first drug for the treatment of narcolepsy. [0003] At present, the synthesis of reported 2-(diphenylmethylsulfinyl)acetamide all starts from diphenylmethanol. Decomposition, oxidation and other reactions to obtain products. The process uses the corrosive agent thionyl chloride and the giant drug dimethyl sulfate, and needs to discharge a large amount of industrial was...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C317/44C07C315/00
Inventor 裴文孙莉陶文伟
Owner ZHEJIANG UNIV OF TECH