Thiazolidinedione → 5-(4-Methoxybenzylidene)-thiazolidine-2,4-dione

HRID 1581648Notes

Reaction equation

HRID 1581648 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[S:11]1[CH2:15][C:14](=[O:16])[NH:13][C:12]1=[O:17].N1CCCCC1>C(O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[C:15]2[S:11][C:12](=[O:17])[NH:13][C:14]2=[O:16])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 312444-Methoxybenzaldehyde

Product 1

HCID 2331125-(4-Methoxybenzylidene)-thiazolidine-2,4-dioneYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Methoxybenzaldehyde (20.4 g, 150 mmol), thiazolidine-2,4-dione (21.1 g, 180 mmol), piperidine (12.8 g, 150 mmol) and ethanol (150 mL) were mixed and refluxed for 18 hours. After allowed to stand for cooling, the precipitated crystals were collected by filtration. These were washed with ethanol, and then dried to obtain 11.2 g (32%) of the title compound as yellow crystals. Moreover, the filtrate was made acidic with concentrated hydrochloric acid, and the precipitated crystals were collected by filtration, washed with ethanol and water, and then dried to additionally obtain 18.1 g (51%, totally 83%) of the title compound as yellow crystals.

Workup

  1. temperaturerefluxed for 18 hours
  2. temperaturefor cooling
  3. filtrationthe precipitated crystals were collected by filtration
  4. washThese were washed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-6d75d2ea75dd479499a05eb2ed78447d
Source dataset
uspto-grants-2004_05
Patent number
US06730687B1

Reaction notes

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