Tizolemide, S-730704-B, Hoe-740
噻苯磺胺Chemical Name: 2-Chloro-5-[4-hydroxy-3-methyl-2-(methylimino) 4-thiazolidinyl]benzenesulfonamide; 4-(4-Chloro-3-sulfamoylphenyl)-3-methyl-2-(methylimino)-1,3-thiazolidin-4-ol
CAS No. 56488-58-5
项目整合开发状态: Biological Testing
项目研究机构: Aventis Pharma (Originator)
合成路线:The bromination of 4-chloro-3-sulfamoyl acetophenone (I) with Br2 in ethyl acetate gives 4-chloro-3-sulfamoyl-alpha-bromoacetophenone (II),which is cyclized with N,N'-dimethylthiourea (III) in acetone and finally treated with NaHCO3 in water.
合成路线:The bromination of 4-chloro-3-chlorosulfonylacetophenone (IV) with Br2 in ethyl acetate yields 4-chloro-3-chlorosulfonyl-alpha-bromoacetophenone (V),which is cyclized with N,N'-dimethylthiourea (III) affording 4-(4-chloro-3-chlorosulfonylphenyl)-3-methyl-2-(methylimino)-1,3-thiazolidin-4-ol (VI).Finally,this compound is treated with NH3 in methanol.
合成路线:The reaction of 4-chloro-3-sulfamoyldiazoacetophenone (VII) with HCl in diglyme yields 4alpha-dichloro-3-sulfamoylacetophenone (VIII),which is cyclized with N,N'-dimethylthiourea (III) in acetone.Compound (VIII) can also be obtained by reaction of 4-chloro-3-sulfamoyl-alpha-hydroxyacetophenone (IX) with refluxing SOCl2.
📌 参考资料/链接：
参考文献标题:Tizolemide
文献作者:Mealey,N.E.; Castar,J.; Blancafort,P.; Lesson,P.A.; Serradell,M.N.
参考来源:Drugs Fut 1981,6(6),371
📄 详细内容
合成路线:The bromination of 4-chloro-3-sulfamoyl acetophenone (I) with Br2 in ethyl acetate gives 4-chloro-3-sulfamoyl-alpha-bromoacetophenone (II),which is cyclized with N,N'-dimethylthiourea (III) in acetone and finally treated with NaHCO3 in water.
合成路线:The bromination of 4-chloro-3-chlorosulfonylacetophenone (IV) with Br2 in ethyl acetate yields 4-chloro-3-chlorosulfonyl-alpha-bromoacetophenone (V),which is cyclized with N,N'-dimethylthiourea (III) affording 4-(4-chloro-3-chlorosulfonylphenyl)-3-methyl-2-(methylimino)-1,3-thiazolidin-4-ol (VI).Finally,this compound is treated with NH3 in methanol.
合成路线:The reaction of 4-chloro-3-sulfamoyldiazoacetophenone (VII) with HCl in diglyme yields 4alpha-dichloro-3-sulfamoylacetophenone (VIII),which is cyclized with N,N'-dimethylthiourea (III) in acetone.Compound (VIII) can also be obtained by reaction of 4-chloro-3-sulfamoyl-alpha-hydroxyacetophenone (IX) with refluxing SOCl2.
参考文献标题:
文献作者:Lang,H.J.; Muschaweck,R.
参考来源:US 4061761
产品链接: CAS No. 56488-58-5››