N-(4-acetylphenyl)benzenesulfonamide → 5-[4-(2-{1-[4-(Phenylsulfonylamino)phenyl]ethylideneaminooxy}ethoxy)benzyl]thiazolidine-2,4-dione
Reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17](=O)[CH3:18])=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:21][O:22][CH2:23][CH2:24][O:25][C:26]1[CH:39]=[CH:38][C:29]([CH2:30][CH:31]2[S:35][C:34](=[O:36])[NH:33][C:32]2=[O:37])=[CH:28][CH:27]=1>>[C:1]1([S:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17](=[N:21][O:22][CH2:23][CH2:24][O:25][C:26]3[CH:27]=[CH:28][C:29]([CH2:30][CH:31]4[S:35][C:34](=[O:36])[NH:33][C:32]4=[O:37])=[CH:38][CH:39]=3)[CH3:18])=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
3
Procedure
Following a procedure similar to that described in Example 40(f), 170 mg of 4'-(phenylsulfonylamino)acetophenone were reacted with 197 mg of 5-[4-(2-aminooxyethoxy)benzyl]thiazolidine-2,4-dione hydrochloride [prepared as described in Example 40(e)]. The reaction mixture was then concentrated by evaporation under reduced pressure, and the resulting residue was extracted with ethyl acetate. The extract was washed with water and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 2:98 by volume mixture of methanol and methylene chloride as the eluent, to give 170 mg of the title compound, melting at 213°-215° C.