Dimethylhydantoin → HCID 12112018, compound

HRID 896605Notes

Reaction equation

HRID 896605 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[H-].[Na+].[C:12]1([C:22](Cl)=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.C([O:28][CH2:29][CH3:30])(=O)C>O1CCCC1>[CH3:1][C:2]1([CH3:9])[N:6]([C:22]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)=[O:23])[C:5](=[O:7])[N:4]([C:29]([C:30]2[C:21]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:17]=[CH:18][CH:19]=2)=[O:28])[C:3]1=[O:8]

Participants

6

Reactant 4

HCID 6491DimethylhydantoinHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 701461-Naphthalenecarbonyl chloride

Product 1

HCID 12112018HCID 12112018, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5,5-Dimethylimidazolidine-2,4-dione (1.28 g) was dissolved in tetrahydrofuran (50 mL), and sodium hydride (60%, in oil) (0.80 g) was added at 0° C. under ice-cooling. After stirred for 30 minutes, 1-naphthoyl chloride (3.80 g) was added at 0° C., and the mixture was stirred at room temperature overnight. Ethyl acetate (200 mL) was added to the reaction solution, the mixture 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 1.19 g of white crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature overnight
  3. washthe mixture was washed with a saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customFurther purification by silica gel chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-f89249374503489e98456a780cb07de0
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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