Water → HCID 69731930, compound

HRID 896586Notes

Reaction equation

HRID 896586 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+].[C:22]1([S:32](Cl)(=[O:34])=[O:33])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1.O>O1CCCC1.C(OCC)(=O)C>[C:22]1([S:32]([N:9]2[C:8](=[O:13])[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:11][C:10]2=[O:12])(=[O:34])=[O:33])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 17755,5-DiphenylhydantoinHCID 24758Sodium hydrideHCID 665601-Naphthalenesulfonyl chloride

Product 1

HCID 69731930HCID 69731930, compoundYield 11.4%

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, 1-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. The material was dissolved in ethyl acetate, and purified by silica gel chromatography (hexane:ethyl acetate=3:1 to 2:1) to obtain 100 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. dissolutionThe material was dissolved in ethyl acetate
  8. custompurified by silica gel chromatography (hexane:ethyl acetate=3:1 to 2:1)

Sources & evidence

ORD record
ord-c833fbaa19254655b99da503b57dac06
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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