Thiazolidinedione → 5-(4-Chlorobenzylidene)-2,4-thiazolidinedione

HRID 964142

Reaction equation

HRID 964142 reaction equation
[S:1]1[CH2:5][C:4](=[O:6])[NH:3][C:2]1=[O:7].[Cl:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1.N1CCCCC1>C(O)C>[Cl:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[C:5]2[S:1][C:2](=[O:7])[NH:3][C:4]2=[O:6])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 77264-ChlorobenzaldehydeHCID 8082Piperidine

Product 1

HCID 2330705-(4-Chlorobenzylidene)-2,4-thiazolidinedioneYield 43.4%

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 4-chlorobenzaldehyde 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 17.75 g of the desired compound (43.4% 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-8640849b69ac42fc9173ca6e5bbd63fe
Source dataset
uspto-grants-1998_06
Patent number
US05767121

Linked notes

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