• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【药物名称】Modafinil, CRL-40476, Modavigil, Modasomil, Vigil, Alertec, Provigil, Modiodal

【化学名称】2-[(Diphenylmethyl)sulfinyl]acetamide
      2-(Benzhydrylsulfinyl)acetamide

【CA登记号】68693-11-8

【 分 子 式 】C15H15NO2S

【 分 子 量 】273.3563

【开发单位】Azwell (Orphan Drug), Lafon (Originator), Novartis (Marketer), Azwell (Licensee), Cephalon (Licensee), Dompè(Licensee), Draxis Health (Licensee), Shire Pharmaceuticals (Licensee)

【药理作用】Alzheimer's Dementia, Treatment of , Antidepressants, Antinarcoleptic Drugs, Attention Deficit Hyperactivity Disorder (ADHD), Treatment of, Cognition Disorders, Treatment of, Mood Disorders, Treatment of, NEUROLOGIC DRUGS, Neurologic Drugs (Miscellaneous), PSYCHOPHARMACOLOGIC DRUGS, Sleep Disorders, Treatment of, alpha1-Adrenoceptor Agonists

合成路线1

This compound can be obtained by two related ways: 1) The condensation of benzhydrol (I) with chloroacetic acid (II) by means of thiourea (III) in concentrated hydrobromic acid at 95 C gives 2-(diphenylmethylthio)acetic acid (IV), which by reaction with SOCl2 in refluxing benzene is converted into the acid chloride (V). The reaction of (V) with ammonium hydroxide in water - methylene chloride affords 2-(diphenylmethylthio)acetamide (VI), which is finally oxidized with hydrogen peroxide. 2) Acid (IV) can also be oxidized with hydrogen peroxide to give 2-(diphenylmethylsulfinyl)acetic acid (VII), which is methylated with dimethylsulfate and NaHCO3 to the corresponding methyl ester (VIII). Finally, this compound is treated with ammonia in anhydrous methanol.

1 Lafon, L. (Laboratoires L. Lafon); Acetamide derivs. DE 2809625; FR 2385693; US 4177290 .
2 Prous, J.; Castaner, J.; MODAFINIL. Drugs Fut 1990, 15, 2, 130.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 11845 Diphenylmethanol; Benzhydrol 91-01-0 C13H12O 详情 详情
(II) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(III) 11847 2-Chloroacetic acid; Chloroacetic Acid 79-11-8 C2H3ClO2 详情 详情
(IV) 11848 2-(Benzhydrylsulfanyl)acetic acid C15H14O2S 详情 详情
(V) 11849 2-(Benzhydrylsulfanyl)acetyl chloride C15H13ClOS 详情 详情
(VI) 11850 2-(Benzhydrylsulfanyl)acetamide C15H15NOS 详情 详情
(VII) 11851 2-(Benzhydrylsulfinyl)acetic acid C15H14O3S 详情 详情
(VIII) 11852 methyl 2-(benzhydrylsulfinyl)acetate C16H16O3S 详情 详情
Extended Information