【结 构 式】 |
【分子编号】65088 【品名】6-chloro-2-hydroxy-3-nitrobenzenesulfonamide 【CA登记号】 |
【 分 子 式 】C6H5ClN2O5S 【 分 子 量 】252.63488 【元素组成】C 28.53% H 1.99% Cl 14.03% N 11.09% O 31.67% S 12.69% |
合成路线1
该中间体在本合成路线中的序号:(VI)2,6-Dichlorobenzenethiol (I) is oxidized to the sulfonyl chloride (II) employing N-chlorosuccinimide. Subsequent treatment of acid chloride (II) with ammonia in cold pyridine provides sulfonamide (III). Reaction of (III) with HNO3 in the presence of concentrated H2SO4 leads to the nitro derivative (IV). Then, displacement of one chloride group of (IV) with potassium acetate in the presence of crown ether gives rise to the acetate ester (V), which is further hydrolyzed to phenol (VI) under acidic conditions. Nitro group reduction in (VI) with H2 and Pd/C affords aniline (VII). Finally, coupling of (VII) with 2,3-dichlorophenyl isocyanate (VIII) produces the title diaryl urea.
【1】 Widdowson, K.L.; Jin, Q.; McCleland, B.W.; Palovich, M.R. (GlaxoSmithKline Inc.); Hydroxy diphenyl urea sulfonamides as IL-8 receptor antagonists. EP 1161232; JP 2002532419; US 6500863; WO 0035442 . |
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) | 33293 | 2,6-Dichloro thiophenol; 2,6-Dichlorobenzenethiol; 2,6-Dichlorophenylhydrosulfide | 24966-39-0 | C6H4Cl2S | 详情 | 详情 |
(II) | 65084 | 2,6-dichlorobenzenesulfonyl chloride | C6H3Cl3O2S | 详情 | 详情 | |
(III) | 65085 | 2,6-dichlorobenzenesulfonamide | C6H5Cl2NO2S | 详情 | 详情 | |
(IV) | 65086 | 2,6-dichloro-3-nitrobenzenesulfonamide | C6H4Cl2N2O4S | 详情 | 详情 | |
(V) | 65087 | 2-(aminosulfonyl)-3-chloro-6-nitrophenyl acetate | C8H7ClN2O6S | 详情 | 详情 | |
(VI) | 65088 | 6-chloro-2-hydroxy-3-nitrobenzenesulfonamide | C6H5ClN2O5S | 详情 | 详情 | |
(VII) | 65089 | 3-amino-6-chloro-2-hydroxybenzenesulfonamide | C6H7ClN2O3S | 详情 | 详情 | |
(VIII) | 28667 | 1,2-dichloro-3-isocyanatobenzene | 41195-90-8 | C7H3Cl2NO | 详情 | 详情 |