Thiazolidinedione → HCID 86759063, compound

HRID 1357459Notes

Reaction equation

HRID 1357459 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][Br:8].[S:9]1[CH2:13][C:12](=[O:14])[NH:11][C:10]1=[O:15].C(N(CC)CC)C>C(#N)C>[Br:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:11]1[C:12](=[O:14])[CH2:13][S:9][C:10]1=[O:15]

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8471TriethylamineHCID 123681,6-Dibromohexane

Product 1

HCID 86759063HCID 86759063, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

36.6 g of 1,6-dibromohexane, 5.9 g of 2,4-thiazolidinedione and 7.1 g of triethylamine were added to 125 ml of acetonitrile and the mixture was heated with stirring under reflux for 8 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure and the residue was poured into water. The mixture was extracted with methylene chloride and the methylene chloride layer was washed with saturated brine and dried over sodium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1→4:1) to obtain 9.8 g of the title compound as pale yellow oil (yield: 70%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 8 hours
  3. customthe solvent was evaporated under reduced pressure
  4. additionthe residue was poured into water
  5. extractionThe mixture was extracted with methylene chloride
  6. washthe methylene chloride layer was washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. customAfter the solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1→4:1)

Sources & evidence

ORD record
ord-f78d7c3e2c7f40fcabbafea6af378558
Source dataset
uspto-grants-2003_07
Patent number
US06593323B1

Reaction notes

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