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【结 构 式】 
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【药物名称】CL-259763 【化学名称】N-[4-(4-Fluorophenylsulphonyl)phenyl]acetamide 【CA登记号】734-22-5 【 分 子 式 】C14H12FNO3S 【 分 子 量 】293.31904 |
【开发单位】Wyeth Pharmaceuticals (Originator) 【药理作用】IMMUNOMODULATING AGENTS, Immunomodulators |
合成路线1
1) The reaction of p-fluorothiophenol (I) with p-chloronitrobenzene (II) in 50% aqueous ethanol in the presence of sodium carbonate gives p-fluorophenyl-p-nitrophenyl sulfide (III), which is then oxidized with 30% aqueous hydrogen peroxide in glacial acetic acid to give the corresponding sulfone (IV). The catalytic reduction of the sulfone (IV) with Raney Nickel in p-dioxane affords p-(p-fluorophenylsulfonyl)aniline (V), which is then acetylated with acetic anhydride in tetrahydrofuran to give title compound.
| 【1】 Durr, F.E.; Lang, S.A. Jr.; Shang Wang, B.; Ruszala-Mallon, V.; Lin, Y.-i.; Fields, T.L.; CL-259,763. Drugs Fut 1987, 12, 5, 431. |
| 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) | 22971 | 4-fluorobenzenethiol; 4-fluorophenylhydrosulfide; 4-Fluorothiophenol | 371-42-6 | C6H5FS | 详情 | 详情 |
| (II) | 13909 | 1-Chloro-4-nitrobenzene; p-Nitrochlorobenzene | 100-00-5 | C6H4ClNO2 | 详情 | 详情 |
| (III) | 22973 | 4-fluorophenyl 4-nitrophenyl sulfide; 1-fluoro-4-[(4-nitrophenyl)sulfanyl]benzene | C12H8FNO2S | 详情 | 详情 | |
| (IV) | 22974 | 4-fluorophenyl 4-nitrophenyl sulfone; (4-fluorophenyl)(4-nitrophenyl)dioxo-lambda(6)-sulfane | C12H8FNO4S | 详情 | 详情 | |
| (V) | 22975 | 4-[(4-fluorophenyl)sulfonyl]aniline; 4-[(4-fluorophenyl)sulfonyl]phenylamine | C12H10FNO2S | 详情 | 详情 |
合成路线2
2) The reaction of fluorobenzene (VI) with N-acetylsulfanilyl chloride (VII) in the presence of anhydrous aluminum chloride gives the desired acetamide in one step.
| 【1】 Durr, F.E.; Lang, S.A. Jr.; Shang Wang, B.; Ruszala-Mallon, V.; Lin, Y.-i.; Fields, T.L.; CL-259,763. Drugs Fut 1987, 12, 5, 431. |