Dimethylhydantoin → HCID 22351157, compound

HRID 896607Notes

Reaction equation

HRID 896607 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[H-].[Na+].[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[S:22](Cl)(=[O:24])=[O:23]>O1CCCC1>[CH3:1][C:2]1([CH3:9])[N:6]([S:22]([C:13]2[CH:14]=[CH:15][C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=2)(=[O:24])=[O:23])[C:5](=[O:7])[N:4]([S:22]([C:13]2[CH:14]=[CH:15][C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=2)(=[O:24])=[O:23])[C:3]1=[O:8]

Participants

5

Reactant 3

HCID 6491DimethylhydantoinHCID 71252-Naphthalenesulfonyl chlorideHCID 24758Sodium hydride

Product 1

HCID 22351157HCID 22351157, compoundYield 22.4%

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, 2-naphthalenesulfonyl chloride (2.38 g) was added at 0° C., and the mixture was stirred at room temperature overnight. After the solvent was distilled off, ethyl acetate (150 mL) 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. After drying over anhydrous magnesium sulfate, the solvent was distilled off. Further purification by silica gel chromatography (hexane:ethyl acetate=2:1) afforded 597 mg of white crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature overnight
  3. distillationAfter the solvent was distilled off
  4. additionethyl acetate (150 mL) was added to the reaction solution
  5. washthe solution was washed with 1N hydrochloric acid
  6. dry with materialAfter drying 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-1d8337dd96d9467e80c80d4a4abc4a3e
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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