Acetophenone → 5-{4-[2-(1-Phenylethylideneaminooxy)ethoxy]benzyl}thiazolidine-2,4-dione

HRID 1941673Notes

Reaction equation

HRID 1941673 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].Cl.[NH2:11][O:12][CH2:13][CH2:14][O:15][C:16]1[CH:29]=[CH:28][C:19]([CH2:20][CH:21]2[S:25][C:24](=[O:26])[NH:23][C:22]2=[O:27])=[CH:18][CH:17]=1>>[C:4]1([C:1](=[N:11][O:12][CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:20][CH:21]3[S:25][C:24](=[O:26])[NH:23][C:22]3=[O:27])=[CH:28][CH:29]=2)[CH3:2])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 7410AcetophenoneHCID 218339655-(4-[2-Aminooxyethoxy)benzyl]thiazolidine-2,4-dione hydrochloride

Product 1

HCID 738479915-{4-[2-(1-Phenylethylideneaminooxy)ethoxy]benzyl}thiazolidine-2,4-dione

Procedure

Following a procedure similar to that described in Example 40(f), 0.16 ml of acetophenone was reacted with 400 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 mixed with diisopropyl ether and the mixture was stirred. The precipitated powder was collected by filtration, to give 370 mg of the title compound.

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. additionThe residue was mixed with diisopropyl ether
  6. filtrationThe precipitated powder was collected by filtration

Sources & evidence

ORD record
ord-946851e7b9af4048a260fb089a50a946
Source dataset
uspto-grants-1997_12
Patent number
US05703096

Reaction notes

Loading…