Water → HCID 22351167, compound

HRID 896584Notes

Reaction equation

HRID 896584 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27](Cl)=[O:28].O>O1CCCC1.C(OCC)(=O)C>[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27]([N:9]1[C:8](=[O:13])[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:11][C:10]1=[O:12])=[O:28]

Participants

7

Reactant 4

HCID 962WaterHCID 17755,5-DiphenylhydantoinHCID 24758Sodium hydrideHCID 682422-Furancarbonyl chloride

Product 1

HCID 22351167HCID 22351167, compoundYield 43.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

5,5-Diphenylimidazolidine-2,4-dione (0.5 g) was dissolved in tetrahydrofuran (5 mL), and sodium hydride (60%, in oil) (87 mg) was added at 0° C. under ice-cooling. After stirred for 30 minutes, 2-furoyl chloride (235 mg) was added 0° C., and the mixture was stirred at room temperature for 2.5 hours. After water was added carefully, ethyl acetate (200 mL) was added, and the layers were separated. The resulting organic layer was washed with a saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was distilled off. Further purification by silica gel chromatography (hexane:ethyl acetate=2:1) afforded white powders. The resulting foam was recrystallized from IPE to obtain 273 mg of white crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 2.5 hours
  3. customthe layers were separated
  4. washThe resulting organic layer was washed with a saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customFurther purification by silica gel chromatography (hexane:ethyl acetate=2:1)
  8. customafforded white powders
  9. customThe resulting foam was recrystallized from IPE

Sources & evidence

ORD record
ord-97ed866c24ba46638bae0953246fdd29
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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