5-[6-(5-Methyl-2-phenyl-4-oxazolyl-methoxy)-2-benzofuranylmethylidene]-2,4-thiazolidinedione → 5-[6-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranylmethyl]-2,4-thiazolidinedione

HRID 1049

Reaction equation

HRID 1049 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:31]=[CH:30][C:18]2[CH:19]=[C:20]([CH:22]=[C:23]3[S:27][C:26](=[O:28])[NH:25][C:24]3=[O:29])[O:21][C:17]=2[CH: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:31]=[CH:30][C:18]2[CH:19]=[C:20]([CH2:22][CH:23]3[S:27][C:26](=[O:28])[NH:25][C:24]3=[O:29])[O:21][C:17]=2[CH:16]=1

Participants

4

Reactant 1

HCID 854521775-[6-(5-Methyl-2-phenyl-4-oxazolyl-methoxy)-2-benzofuranylmethylidene]-2,4-thiazolidinedione

Product 1

HCID 867521715-[6-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranylmethyl]-2,4-thiazolidinedioneYield 38%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-[6-(5-methyl-2-phenyl-4-oxazolyl-methoxy)-2-benzofuranylmethylidene]-2,4-thiazolidinedione (0.80 g), palladium-carbon (5%, 1.60 g) and tetrahydrofuran (250 ml) was subjected to catalytic reduction at room temperature under a hydrogen pressure of 3.2 kgf/cm2 for 8 hours. After the catalyst was filtered off, the filtrate was subjected to catalytic reduction under constant conditions for additional 16 hours. After the catalyst was filtered off, the filtrate was concentrated under reduced pressure; the residue was subjected to silica gel column chromatography. From the fraction eluted with ethyl acetate-chloroform (1:5, v/v), crystals of 5-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranylmethyl]-2,4-thiazolidinedione (0.305 g, 38%) were obtained, which was then recrystallized from dichloromethane-methanol to yield yellow needles having a melting point of 179° to 180° C.

Workup

  1. customwas subjected to catalytic reduction at room temperature under a hydrogen
  2. customfor 8 hours
  3. filtrationAfter the catalyst was filtered off
  4. filtrationAfter the catalyst was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. washFrom the fraction eluted with ethyl acetate-chloroform (1:5

Sources & evidence

ORD record
ord-f01dc9a32ad94d4099a32d40a2b8c964
Source dataset
uspto-grants-1998_03
Patent number
US05723479

Linked notes

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