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【结 构 式】 
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【分子编号】60755 【品名】N-[2-nitro-5-(phenylsulfanyl)phenyl]acetamide 【CA登记号】 |
【 分 子 式 】C14H12N2O3S 【 分 子 量 】288.32696 【元素组成】C 58.32% H 4.19% N 9.72% O 16.65% S 11.12% |
合成路线1
该中间体在本合成路线中的序号：(III)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 |