Water → HCID 22351170, compound

HRID 896585Notes

Reaction equation

HRID 896585 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+].[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1[S:32](Cl)(=[O:34])=[O:33].O>O1CCCC1.C(OCC)(=O)C>[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1[S:32]([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:33])=[O:34]

Participants

7

Reactant 4

HCID 962WaterHCID 17755,5-DiphenylhydantoinHCID 71252-Naphthalenesulfonyl chlorideHCID 24758Sodium hydride

Product 1

HCID 22351170HCID 22351170, compoundYield 36.5%

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-naphthalenesulfonyl chloride (471 mg) was added at 0° C., and the mixture was stirred at room temperature overnight. After water was added carefully, ethyl acetate (100 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=3:1 to 2:1) afforded 320 mg of white powder.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature overnight
  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=3:1 to 2:1)

Sources & evidence

ORD record
ord-8a572489390743bdaa8b7e8e8aa1f5eb
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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