Acetic Acid → 5-([4-[2-(4-(2-Propanesulfonyloxy)phenyl)ethoxy]phenyl]methyl)thiazolidine-2,4-dione

HRID 1595528Notes

Reaction equation

HRID 1595528 reaction equation
[CH3:1][CH:2]([S:4]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][O:16][C:17]2[CH:30]=[CH:29][C:20]([CH:21]=[C:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=2)=[CH:10][CH:9]=1)(=[O:6])=[O:5])[CH3:3].C(O)(=O)C>C(OCC)(=O)C.[Pd]>[CH3:3][CH:2]([S:4]([O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][O:16][C:17]2[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=2)=[CH:12][CH:13]=1)(=[O:6])=[O:5])[CH3:1]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 867573785-(4-[2-(4-(2-Propanesulfonyloxy)phenyl)ethoxy]benzylidene)thiazolidine-2,4-dione

Product 1

HCID 867573795-([4-[2-(4-(2-Propanesulfonyloxy)phenyl)ethoxy]phenyl]methyl)thiazolidine-2,4-dioneYield 45.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1.2 g (2.7 mmole) 5-(4-[2-(4-(2-propanesulfonyloxy)phenyl)ethoxy]benzylidene)thiazolidine-2,4-dione was dissolved in 250 ml ethyl acetate by heating. 6 ml acetic acid and 1 g Pd/C (5%) were added and the hydrogenation was started while the solution was warm. After 12 hours at room temperature, more of the catalyst was added. After 60 hours the reaction mixture was filtered through celite and the solvent was evaporated in vacuo. The hydrogenation was restarted with more Pd/C (10%) and ethyl acetate. After 6 hours the reaction mixture was filtered through celite and the solvent was evaporated in vacuo. The crude product was purified by chromatography on silica gel using dichloromethane:methanol (95:5) as eluent to give 0.557 g (yield 45.9%) of the desired product.

Workup

  1. temperatureby heating
  2. temperaturewas warm
  3. additionmore of the catalyst was added
  4. filtrationAfter 60 hours the reaction mixture was filtered through celite
  5. customthe solvent was evaporated in vacuo
  6. filtrationAfter 6 hours the reaction mixture was filtered through celite
  7. customthe solvent was evaporated in vacuo
  8. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-caf7adcf92dc4616b420cb6209f8c734
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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