5-(4-[2-Aminooxyethoxy)benzyl]thiazolidine-2,4-dione hydrochloride → 5-[4-(2-{1-[4-(2-Pyridylsulfonyl)phenyl]ethylideneaminooxy}ethoxy)benzyl]thiazolidine-2,4-dione

HRID 1741330Notes

Reaction equation

HRID 1741330 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16](=O)[CH3:17])=[CH:12][CH:11]=1)(=[O:9])=[O:8].Cl.[NH2:20][O:21][CH2:22][CH2:23][O:24][C:25]1[CH:38]=[CH:37][C:28]([CH2:29][CH:30]2[S:34][C:33](=[O:35])[NH:32][C:31]2=[O:36])=[CH:27][CH:26]=1>>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16](=[N:20][O:21][CH2:22][CH2:23][O:24][C:25]2[CH:26]=[CH:27][C:28]([CH2:29][CH:30]3[S:34][C:33](=[O:35])[NH:32][C:31]3=[O:36])=[CH:37][CH:38]=2)[CH3:17])=[CH:12][CH:11]=1)(=[O:9])=[O:8]

Participants

3

Reactant 2

HCID 218339655-(4-[2-Aminooxyethoxy)benzyl]thiazolidine-2,4-dione hydrochlorideHCID 218339884'-(2-Pyridylsulfonyl)acetophenone

Product 1

HCID 867518225-[4-(2-{1-[4-(2-Pyridylsulfonyl)phenyl]ethylideneaminooxy}ethoxy)benzyl]thiazolidine-2,4-dioneYield 61.3%

Procedure

Following a procedure similar to that described in Example 40(f), 150 mg of 4'-(2-pyridylsulfonyl)-acetophenone were reacted with 183 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 185 mg of the title compound as a gum.

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-c5a032a593bb41b5b340f6fe6a16c01a
Source dataset
uspto-grants-1999_10
Patent number
US05972959

Reaction notes

Loading…