Thiazolidinedione → HCID 53796424, compound

HRID 1729050Notes

Reaction equation

HRID 1729050 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][S:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.[S:23]1[CH2:27][C:26](=[O:28])[NH:25][C:24]1=[O:29].N1CCCCC1>C(O)C.CCOCC>[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][S:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[C:27]2[S:23][C:24](=[O:29])[NH:25][C:26]2=[O:28])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 19013410HCID 19013410, compound

Product 1

HCID 53796424HCID 53796424, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

4-[(5-Methyl-2-phenyl-4-oxazolyl)methylthio]benzaldehyde (0.05 mol), thiazolidine-2,4-dione (11.7 g, 0.10 mol and piperidine (0.85 g, 0.01 mol)are combined in 300 mL absolute ethanol, and the mixture refluxed for 24 hours, cooled to 0° C., diluted slowly with 600 mL of ether and, after stirring for 1 hour at 0° C. present title recovered by filtration. If desired, the product is triturated with 150 mL of warm acetic acid (40°-50° C.). The resulting slurry is cooled to room temperature, diluted with 300 mL of ether, and purified title productrecovered by filtration.

Workup

  1. temperaturethe mixture refluxed for 24 hours
  2. filtrationrecovered by filtration
  3. customthe product is triturated with 150 mL of warm acetic acid (40°-50° C.)
  4. temperatureThe resulting slurry is cooled to room temperature
  5. additiondiluted with 300 mL of ether
  6. custompurified title
  7. filtrationproductrecovered by filtration

Sources & evidence

ORD record
ord-5f8c011003694bdab8b43bd872b1785e
Source dataset
uspto-grants-1994_07
Patent number
US05330998

Reaction notes

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