N-(4-acetylphenyl)benzenesulfonamide → 5-[4-(2-{1-[4-(Phenylsulfonylamino)phenyl]ethylideneaminooxy}ethoxy)benzyl]thiazolidine-2,4-dione

HRID 1741332Notes

Reaction equation

HRID 1741332 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]=1

Participants

3

Reactant 2

HCID 682447N-(4-acetylphenyl)benzenesulfonamideHCID 218339655-(4-[2-Aminooxyethoxy)benzyl]thiazolidine-2,4-dione hydrochloride

Product 1

HCID 867518245-[4-(2-{1-[4-(Phenylsulfonylamino)phenyl]ethylideneaminooxy}ethoxy)benzyl]thiazolidine-2,4-dioneYield 51%

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.

Workup

  1. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  2. extractionthe resulting residue was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified by column chromatography through silica gel
  6. additionby volume mixture of methanol and methylene chloride as the eluent

Sources & evidence

ORD record
ord-412d97185f844c76887a42450707ff47
Source dataset
uspto-grants-1999_10
Patent number
US05972959

Reaction notes

Loading…