Dimethylhydantoin → HCID 69731520, compound

HRID 896591Notes

Reaction equation

HRID 896591 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([S:22](Cl)(=[O:24])=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1>O1CCCC1>[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[N:4]([S: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:24])=[O:23])[C:3]1=[O:8]

Participants

5

Reactant 3

HCID 6491DimethylhydantoinHCID 24758Sodium hydrideHCID 665601-Naphthalenesulfonyl chloride

Product 1

HCID 69731520HCID 69731520, compoundYield 11.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5,5-Dimethylimidazolidine-2,4-dione (1.28 g) was dissolved in tetrahydrofuran (20 mL), and sodium hydride (60%, in oil) (0.25 g) was added at 0° C. under ice-cooling. After stirred for 30 minutes, 1-naphthalene sulfonyl chloride (2.38 g) was added at 0° C., and the mixture was stirred at room temperature overnight. After the solvent was distilled off, 150 mL of ethyl acetate was added to the reaction solution, and the solution was washed with 1N hydrochloric acid, an aqueous saturated sodium bicarbonate solution and a saturated brine in turn. The solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off. Further purification by silica gel chromatography (hexane:ethyl acetate=2:1) afforded 369 mg of white crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature overnight
  3. distillationAfter the solvent was distilled off
  4. addition150 mL of ethyl acetate was added to the reaction solution
  5. washthe solution was washed with 1N hydrochloric acid
  6. dry with materialThe solution was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customFurther purification by silica gel chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-cf27f6587b534aaa81a5f3c2233994f2
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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