Benzaldehyde → 5-Benzylidene-2,4-thiazolidinedione
Reaction equation
[S:1]1[CH2:5][C:4](=[O:6])[NH:3][C:2]1=[O:7].[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1CCCCC1>C(O)C>[CH:8](=[C:5]1[S:1][C:2](=[O:7])[NH:3][C:4]1=[O:6])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 20 g (171 mmol) of 2,4-thiazolidinedione and 17.4 ml (171 mmol) of benzaldehyde 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 31.67 g of the desired compound (90.4% 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-f99fd64ecadc4d6fbfc0db3ce5607ef8
- Source dataset
- uspto-grants-1993_09
- Patent number
- US05246948
Reaction notes
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