Thiazolidinedione → 5-(3,5-Di-tert-butyl-4-hydroxyphenyl)-methylene-2,4-thiazolidinedione

HRID 6174

Reaction equation

HRID 6174 reaction equation
[S:1]1[CH2:5][C:4](=[O:6])[NH:3][C:2]1=[O:7].[C:8]([C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])C=O)([CH3:11])([CH3:10])[CH3:9].N1CCCC[CH2:26]1>C(O)C>[C:21]([C:18]1[CH:17]=[C:14]([CH:5]2[S:1](=[CH2:26])[C:2](=[O:7])[NH:3][C:4]2=[O:6])[CH:13]=[C:12]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:19]=1[OH:20])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehyde

Product 1

HCID 867472385-(3,5-Di-tert-butyl-4-hydroxyphenyl)-methylene-2,4-thiazolidinedioneYield 424.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 12.5 g (107 mmol) of 2,4-thiazolidinedione and 25.0 g (107 mmol) of 3,5-di-tert-butyl-4-hydroxybenzaldehyde in 300 ml of ethanol, 1.05 ml (10.7 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 15.23 g of the desired compound (42.8% 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-06a787a9c29b4bc098767573585c59cc
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Linked notes

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