Benzaldehyde → 5-Benzylidene-2-thioxothiazolidin-4-one

HRID 6170

Reaction equation

HRID 6170 reaction equation
[S:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[S:3].[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1CCCCC1>C(O)C>[CH:8](=[C:7]1[S:1][C:2](=[S:3])[NH:4][C:5]1=[O:6])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8082PiperidineHCID 1201546Rhodanine

Product 1

HCID 28316115-Benzylidene-2-thioxothiazolidin-4-oneYield 66.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 10 g (75.1 mmol) of rhodanine and 7.63 ml (75.1 mmol) of benzaldehyde in 150 ml of ethanol, 0.74 ml (7.5 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 11.07 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-d824881d53434cb8beb91cc10043c497
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Linked notes

Loading…