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

HRID 1956938Notes

Reaction equation

HRID 1956938 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-dfaeb4e531354692b5bfb2d1bd487ce8
Source dataset
uspto-grants-1998_07
Patent number
US05780490

Reaction notes

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