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

HRID 247869Notes

Reaction equation

HRID 247869 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>O>[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

6

Reactant 4

HCID 176Acetic AcidHCID 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 26.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3,5-di-t-butyl-4-hydroxybenzaldehyde (6.5 g, 27 mmoles), 2,4-thiazolidinedione (3.0 g, 26 mmoles), sodium acetate (7.6 g, 93 mmoles), and acetic acid (40 ml) is stirred under an inert atmosphere and heated to reflux. After 78 hours the mixture is stirred into water (300 ml), and the precipitate is filtered off, rinsed three times with water, dried, and recrystallized from ethanol. The product is stirred in 1N NaOH (50 ml) and extracted several times with dichloromethane. The aqueous solution is acidified with acetic acid, stirred for 1-2 hours, and the precipitate is filtered off, rinsed three times with water and dried to afford the pure product (2.3 g), mp 238°-240° C.

Workup

  1. temperatureheated to reflux
  2. filtrationthe precipitate is filtered off
  3. washrinsed three times with water
  4. customdried
  5. customrecrystallized from ethanol
  6. stirringThe product is stirred in 1N NaOH (50 ml)
  7. extractionextracted several times with dichloromethane
  8. stirringstirred for 1-2 hours
  9. filtrationthe precipitate is filtered off
  10. washrinsed three times with water
  11. customdried

Sources & evidence

ORD record
ord-9e00df5029fb4e9c8bdf12a3126f1ac4
Source dataset
uspto-grants-1993_05
Patent number
US05208250

Reaction notes

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