332235, SB-332235
6-氯-3-[[[[((2,3-二氯苯基)氨基]羰基]氨基]-2-羟基苯磺酰胺Chemical Name: 6-Chloro-3-[3-(2,3-dichlorophenyl)ureido]-2-hydroxybenzenesulfonamide
CAS No. 276702-15-9, 276700-98-2 (K salt), 276700-41-5 (Na salt)
项目整合开发状态: Phase I
项目研究机构: GlaxoSmithKline (Originator)
合成路线: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.(1,2)
📌 参考资料/链接：
参考文献标题:Hydroxy diphenyl urea sulfonamides as IL-8 receptor antagonists
文献作者:Widdowson,K.L.; Jin,Q.; McCleland,B.W.; Palovich,M.R.(GlaxoSmithKline Inc.)
参考来源:EP 1161232; JP 2002532419; US 6500863; WO 0035442
📄 详细内容
合成路线: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.(1,2)
参考文献标题:Methods of synthesizing phenol-containing cpds.
文献作者:Widdowson,K.L.; Palovich,M.R.(GlaxoSmithKline Inc.)
参考来源:EP 1383488; WO 0279122
产品链接: CAS No. 276702-15-9››