Ethanol → HCID 23069953, compound

HRID 644462Notes

Reaction equation

HRID 644462 reaction equation
[OH-].[Na+].[S:3]1[CH2:7][C:6](=[O:8])[NH:5][C:4]1=[O:9].[F:10][C:11]([F:25])([F:24])[C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1)[CH2:15]Br.C(O)C>O>[F:10][C:11]([F:24])([F:25])[C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([C:20]([F:23])([F:21])[F:22])[CH:19]=1)[CH2:15][N:5]1[C:6](=[O:8])[CH2:7][S:3][C:4]1=[O:9]

Participants

6

Reactant 4

HCID 702EthanolHCID 5437ThiazolidinedioneHCID 14798Sodium HydroxideHCID 1225733,5-Bis(trifluoromethyl)benzyl bromide

Product 1

HCID 23069953HCID 23069953, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5N Aqueous sodium hydroxide (0.5 mL) was added to a mixture of 2,4-thiazolidinedione (198.7 mg, 1.69 mmol), 3,5-bis(trifluoromethyl)benzyl bromide (0.50 g, 1.63 mmol) and ethanol (5 mL), and the mixture was refluxed for 4 hours. After the reaction mixture was cooled to room temperature, it was poured into water and extracted with ethyl acetate. After the ethyl acetate layer was washed with brine and dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:1→2:1) to give the title compound (405.6 mg, 72.5%) as a white crystal.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. extractionextracted with ethyl acetate
  3. washAfter the ethyl acetate layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe residue obtained by evaporation of the solvent under reduced pressure
  6. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:1→2:1)

Sources & evidence

ORD record
ord-8dd0d32d345445009fcb1238c84039ae
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

Loading…