HCID 54257642, compound → HCID 86749242, compound

HRID 2395694Notes

Reaction equation

HRID 2395694 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[C:22]2[S:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[CH:17][N:16]=1>[C].[Pd].O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]2[S:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[CH:17][N:16]=1

Participants

4

Reactant 1

HCID 54257642HCID 54257642, compound

Product 1

HCID 86749242HCID 86749242, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-[[2-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-pyridyl]methylidene]-2,4-thiazolidinedione (1.00 g), palladium-carbon (5%, 1.00 g) and tetrahydrofuran (80 ml) was subjected to catalytic reduction at room temperature and 1 atom for 6 hours. The catalyst was filtered off, and palladium-carbon (2.00 g) was added and the mixture was further subjected to catalytic reduction at room temperature and 1 atom for 6 hours. The catalyst was filtered off. The filtrate was evaporated under reduced pressure and the residue was subjected to silica gel column chromatography. From the fraction eluted with 2% methanol-chloroform, crystals (520 mg, 52%) of 5-[[2-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-pyridyl]methyl]-2,4-thiazolidinedione were obtained. Recrystallization from dichloromethane-isopropyl ether gave colorless prisms. Melting point: 151°-152° C.

Workup

  1. customwas subjected to catalytic reduction at room temperature
  2. filtrationThe catalyst was filtered off
  3. additionpalladium-carbon (2.00 g) was added
  4. customwas further subjected to catalytic reduction at room temperature
  5. wait1 atom for 6 hours
  6. filtrationThe catalyst was filtered off
  7. customThe filtrate was evaporated under reduced pressure
  8. washFrom the fraction eluted with 2% methanol-chloroform

Sources & evidence

ORD record
ord-4f881a5314c34e3b836cafed2625b8c7
Source dataset
uspto-grants-1996_02
Patent number
US05489602

Reaction notes

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