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【结 构 式】

【药物名称】Oxfendazole, RS-8858

【化学名称】N-[5-(Phenylsulfinyl)-1H-benzimidazol-2-yl]carbamic acid methyl ester

【CA登记号】53716-50-0

【 分 子 式 】C15H13N3O3S

【 分 子 量 】315.35316

【开发单位】

【药理作用】 

合成路线1

The reaction of 4-chloro-2-amino-1-nitrobenzene (I) with sodium phenylmercaptide (A) in DMF gives 2-amino-4-phenylthio-1-nitrobenzene (II), which is treated with acetic anhydride to yield 2-acetamido-4-phenylthio-1-nitrobenzene (III). This product is oxidized with peracetic acid in methanol giving 2-amino-4-phenylsulfinyl-1-nitrobenzene (V). Then the nitro group is reduced with H2 over Pd/C in methanol yielding 1,2-diamino-4-phenylsulfinylbenzene (VI). This product is finally condensed with N,N'-bis(methoxycarbonyl)-S-methylisothiourea (VII) in ethanol - water - acetic acid. The isothiourea (VII) is obtained by reaction of S-methylisothiouronium sulfate (VIII) with methyl chloroformate (B) by means of KOH in water

1 Beard, C.C.; et al. (Syntex, Inc.); DE 2363351 .
2 Castaner, J.; Bogan, J.A.; Oxfendazole. Drugs Fut 1976, 1, 9, 438.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 16993 methyl chlorocarbonate;Carbonochloridic acid methyl ester;[(chlorocarbonyl)oxy]methane;methyl chloroformate 79-22-1 C2H3ClO2 详情 详情
(A) 60753 sodium benzenethiolate C6H5NaS 详情 详情
(I) 15709 5-chloro-2-nitrophenylamine; 5-chloro-2-nitroaniline 1635-61-6 C6H5ClN2O2 详情 详情
(II) 60754 2-nitro-5-(phenylsulfanyl)aniline; 2-nitro-5-(phenylsulfanyl)phenylamine C12H10N2O2S 详情 详情
(III) 60755 N-[2-nitro-5-(phenylsulfanyl)phenyl]acetamide C14H12N2O3S 详情 详情
(IV) 60756 N-[2-nitro-5-(phenylsulfinyl)phenyl]acetamide C14H12N2O4S 详情 详情
(V) 60757 2-nitro-5-(phenylsulfinyl)aniline; 2-nitro-5-(phenylsulfinyl)phenylamine C12H10N2O3S 详情 详情
(VI) 60758 4-(phenylsulfinyl)-1,2-benzenediamine; 2-amino-4-(phenylsulfinyl)phenylamine C12H12N2OS 详情 详情
(VII) 28696 methyl (Z)-[(methoxycarbonyl)amino](methylsulfanyl)methylidenecarbamate C6H10N2O4S 详情 详情
(VIII) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情
Extended Information