Thiazolidinedione → HCID 86754591, compound

HRID 1739014Notes

Reaction equation

HRID 1739014 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:24]=[CH:23][CH:22]=[CH:21][C:16]=1[CH:17]=[CH:18][CH:19]=O.[S:25]1[CH2:29][C:28](=[O:30])[NH:27][C:26]1=[O:31].N1CCCCC1>C(O)(=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=1[CH2:17][CH2:18][CH2:19][CH:29]1[S:25][C:26](=[O:31])[NH:27][C:28]1=[O:30]

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 53705566HCID 53705566, compound

Product 1

HCID 86754591HCID 86754591, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamaldehyde (2.00 g), 2,4-thiazolidinedione (1.10 g), piperidine (0.267 g) and acetic acid (15 ml) was heated under reflux for 2.5 hours. The reaction mixture was concentrated under reduced pressure. Crystals (1.64 g) of 5-[2-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamilidene]-2,4-thiazolidinedione which was precipitated by addition of saturated aqueous sodium bicarbonate solution was collected by filtration and washed with ether. The crystals were dissolved in tetrahydrofuran (150 ml), and 5% palladium-carbon (1.64 g) was added. The mixture was subjected to catalytic hydrogenation at room temperature at a hydrogen pressure of 3.4 kgf/cm2. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure to give crystals. The crystals were recrystallized from dichloromethane-methanol to give 5-[3-[2-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-propyl]-2,4-thiazolidinedione (0.742 g, 34%). White crystals, mp. 173-174° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customCrystals (1.64 g) of 5-[2-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamilidene]-2,4-thiazolidinedione which was precipitated by addition of saturated aqueous sodium bicarbonate solution
  5. filtrationwas collected by filtration
  6. washwashed with ether
  7. dissolutionThe crystals were dissolved in tetrahydrofuran (150 ml)
  8. addition5% palladium-carbon (1.64 g) was added
  9. customwas subjected to catalytic hydrogenation at room temperature at a hydrogen pressure of 3.4 kgf/cm2
  10. filtrationThe catalyst was filtered off
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customto give crystals
  13. customThe crystals were recrystallized from dichloromethane-methanol

Sources & evidence

ORD record
ord-1d076a727cba4b7a89d3199d5c7b13b2
Source dataset
uspto-grants-1999_10
Patent number
US05965589

Reaction notes

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