Thiazolidinedione → 2,4-Thiazolidinedione, 5-(2-thienylmethylene)-, (Z)-
Reaction equation
[S:1]1[CH2:5][C:4](=[O:6])[NH:3][C:2]1=[O:7].[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]=O.N1CCCCC1>C(O)C>[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]=[C:5]1[S:1][C:2](=[O:7])[NH:3][C:4]1=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 20 g (171 mmol) of 2,4-thiazolidinedione and 16.0 ml (171 mmol) of 2-thiophenecarboxaldehyde in 350 ml of ethanol, 1.68 ml (17.1 mmol) of piperidine was added, and the mixture was heated under reflux for 5 hours. After cooling, the precipitated crystals were filtered and washed with cooled ethanol to give 24.03 g of the desired compound (66.6% yield, pale yellow crystals).
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 5 hours
- temperatureAfter cooling
- filtrationthe precipitated crystals were filtered
- washwashed with cooled ethanol
Sources & evidence
- ORD record
- ord-a8002c74e77d49bda9abedb58493cb34
- Source dataset
- uspto-grants-1995_10
- Patent number
- US05457106
Reaction notes
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