Water → HCID 69732453, compound

HRID 896595Notes

Reaction equation

HRID 896595 reaction equation
[C:1]1([C:11]([N:13]2[C:17](=[O:18])[C:16]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[NH:15][C:14]2=[O:31])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:34]I.O>CN(C=O)C>[CH3:34][N:15]1[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:17](=[O:18])[N:13]([C:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)=[O:12])[C:14]1=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12112009HCID 12112009, compound

Product 1

HCID 69732453HCID 69732453, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Naphthylcarbonyl-5,5-diphenylimidazolidine-2,4-dione (100 mg) was dissolved in DMF (4 mL), and sodium hydride (60%, in oil) (10 mg) was added at 0° C. under ice-cooling. After stirred for 30 minutes, methyl iodide (37 mg) was added at 0° C., and the mixture was stirred at room temperature overnight. Water (100 mL) was added to the reaction solution, and separated out white precipitates were filtered. Further recrystallization using hexane:ethyl acetate=1:1 afforded 64 mg of white crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature overnight
  3. customseparated out white
  4. customprecipitates
  5. filtrationwere filtered
  6. customFurther recrystallization

Sources & evidence

ORD record
ord-3904369abf714350a4b30296254a0bce
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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