HCID 3607913, compound → HCID 2818127, compound

HRID 1648454Notes

Reaction equation

HRID 1648454 reaction equation
[C:1]([O:4][C:5]1[CH:18]=[CH:17][C:8]([CH:9]=[C:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[H][H]>C(O)(=O)C.[Pd]>[C:1]([O:4][C:5]1[CH:18]=[CH:17][C:8]([CH2:9][CH:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 3607913HCID 3607913, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 2818127HCID 2818127, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

2.0 g of 5-(4-acetoxybenzylidene)thiazolidine-2,4-dione [prepared as described in step (a) above] were dissolved in 80 ml of acetic acid and the mixture was hydrogenated by passing hydrogen at atmospheric pressure through the solution at 90° C. for 5 hours in the presence of 2.0 g of 10% w/w palladium-on-charcoal. At the end of this time, the catalyst was filtered off, and the filtrate was diluted with toluene. The acetic acid solvent was then removed by distillation as a toluene azeotrope. The crystals which separated out on adding toluene and hexane to the concentrate were collected by filtration and dried to give 1.8 g of the title compound, melting at between 115° C. and 117° C.

Workup

  1. customat 90° C.
  2. customfor 5 hours
  3. filtrationAt the end of this time, the catalyst was filtered off
  4. additionthe filtrate was diluted with toluene
  5. customThe acetic acid solvent was then removed by distillation as a toluene azeotrope
  6. customThe crystals which separated out
  7. additionon adding toluene and hexane to the concentrate
  8. filtrationwere collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-3f57a668387a42a1a9410e388ce9be12
Source dataset
uspto-grants-1995_07
Patent number
US05436257

Reaction notes

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