Thiazolidinedione → HCID 11011837, compound

HRID 1739018Notes

Reaction equation

HRID 1739018 reaction equation
[CH:1]([O:4][C:5]1[CH:14]=[CH:13][C:8]([CH:9]=[CH:10][CH:11]=O)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[S:15]1[CH2:19][C:18](=[O:20])[NH:17][C:16]1=[O:21].N1CCCCC1>C(O)(=O)C>[CH:1]([O:4][C:5]1[CH:14]=[CH:13][C:8]([CH2:9][CH2:10][CH2:11][CH:19]2[S:15][C:16](=[O:21])[NH:17][C:18]2=[O:20])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 54165538HCID 54165538, compound

Product 1

HCID 11011837HCID 11011837, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-isopropoxycinnamaldehyde (6.00 g), 2,4-thiazolidinedione (5.54 g), piperidine (2.69 g) and acetic acid (30 ml) was heated under reflux for 5 hours. The reaction mixture was concentrated under reduced pressure to give precipitated crystals of 5-(4-isopropoxycinnamylidene)-2,4-thiazolidinedione, and the crystals (4.40 g) were collected by filtration and washed with ethyl acetate. The crystals were dissolved in tetrahydrofuran (100 ml), 5% palladium-carbon (2.20 g) was added, and the mixture was subjected to catalytic hydrogenation at room temperature at a hydroaen pressure of 3.8 kgf/cm2. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with ethyl acetate-chloroform (1:9, v/v) gave 5-[3-(4-isopropoxyphenyl)propyl]-2,4-thiazolidinedione (3.61 g, 39%) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customto give
  5. customprecipitated crystals of 5-(4-isopropoxycinnamylidene)-2,4-thiazolidinedione
  6. filtrationthe crystals (4.40 g) were collected by filtration
  7. washwashed with ethyl acetate
  8. dissolutionThe crystals were dissolved in tetrahydrofuran (100 ml)
  9. addition5% palladium-carbon (2.20 g) was added
  10. customwas subjected to catalytic hydrogenation at room temperature at a hydroaen pressure of 3.8 kgf/cm2
  11. filtrationThe catalyst was filtered off
  12. concentrationthe filtrate was concentrated under reduced pressure
  13. washThe fractions eluted with ethyl acetate-chloroform (1:9, v/v)

Sources & evidence

ORD record
ord-841815070cdc468a927ddc0de98e719c
Source dataset
uspto-grants-1999_10
Patent number
US05965589

Reaction notes

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