Thiazolidinedione → 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2,4-thiazolidinedione

HRID 612994Notes

Reaction equation

HRID 612994 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[S:18]1[CH2:22][C:21](=[O:23])[NH:20][C:19]1=[O:24].C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH3:16][C:14]([C:11]1[CH:10]=[C:7]([CH:8]=[C:22]2[S:18][C:19](=[O:24])[NH:20][C:21]2=[O:23])[CH:6]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[C:12]=1[OH:13])([CH3:15])[CH3:17]

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 517045Sodium Acetate

Product 1

HCID 1987265-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2,4-thiazolidinedioneYield 64.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a flask containing 41.7 g (0.18 moles) of 3,5-di-tert-butyl-4-hydroxybenzaldehyde, 25 g (0.21 moles) of 2,4-thiazolidinedione and 29.5 g (0.36 moles) of anhydrous sodium acetate were added. To these solids 175 ml of glacial acetic acid was added and the mixture was stirred and refluxed for 18 hours. The mixture was allowed to cool to room temperature and the precipitated solid was collected by filtration. The precipitate was rinsed with 1:1 water/ethanol then dried. The dried solid was slurried in 300 ml of methylene chloride for five hours, then collected and dried to yield 38.7 g of the sub-titled intermediate.

Workup

  1. additionwere added
  2. temperaturerefluxed for 18 hours
  3. filtrationthe precipitated solid was collected by filtration
  4. washThe precipitate was rinsed with 1:1 water/ethanol
  5. customthen dried
  6. customcollected
  7. customdried

Sources & evidence

ORD record
ord-54c1162cbb884b8e99eed9ab3b699091
Source dataset
uspto-grants-1999_12
Patent number
US06005142

Reaction notes

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