Benzaldehyde → 5-Benzylidene-2,4-thiazolidinedione

HRID 864007

Reaction equation

HRID 864007 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]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5437ThiazolidinedioneHCID 8082Piperidine

Product 1

HCID 1991545-Benzylidene-2,4-thiazolidinedioneYield 90.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitated crystals were filtered
  5. washwashed with cooled ethanol

Sources & evidence

ORD record
ord-52a3ee0448364d61b5db3e794f6507cb
Source dataset
uspto-grants-1996_10
Patent number
US05561147

Linked notes

Loading…