Thiazolidinedione → 2,4-Thiazolidinedione, 5-(2-thienylmethylene)-, (Z)-

HRID 864010

Reaction equation

HRID 864010 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

HCID 5437ThiazolidinedioneHCID 73642-ThiophenecarboxaldehydeHCID 8082Piperidine

Product 1

HCID 36416932,4-Thiazolidinedione, 5-(2-thienylmethylene)-, (Z)-Yield 66.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  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-fa68da6f6f044f40a38315cee62d37be
Source dataset
uspto-grants-1996_10
Patent number
US05561147

Linked notes

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