Dimethylhydantoin → HCID 22351183, compound

HRID 896590Notes

Reaction equation

HRID 896590 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])[NH:6][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 22351183HCID 22351183, compoundYield 7.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.28 g of 5,5-dimethylimidazolidine-2,4-dione 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 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 white crystals. The resulting fraction was recrystallized from IPE to obtain 232 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. washwashed 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)
  9. customafforded white crystals
  10. customThe resulting fraction was recrystallized from IPE

Sources & evidence

ORD record
ord-bce66e85b47840d295c611f48a972d14
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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