Ethyl Acetate → HCID 69732015, compound

HRID 896596Notes

Reaction equation

HRID 896596 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+].C[CH:35](I)[CH:36]([CH3:38])[CH3:37].C(OCC)(=O)C>CN(C=O)C>[CH2:35]([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])[CH:36]([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 5195442-Iodo-3-methylbutaneHCID 12112009HCID 12112009, compound

Product 1

HCID 69732015HCID 69732015, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Naphthylcarbonyl-5,5-diphenylimidazolidine-2,4-dione (51 mg) was dissolved in DMF (0.4 mL), and sodium hydride (60%, in oil) (5 mg) was added. Then, methylisobutyl iodide (23 mg) was added, and the mixture was stirred at room temperature overnight. Ethyl acetate (9.5 mL) was added to the reaction solution, separated out white precipitates were filtered, and the filtrate was concentrated and purified by silica gel chromatography (hexane:ethyl acetate=2:1) to obtain 20 mg of white crystals.

Workup

  1. customseparated out white
  2. customprecipitates
  3. filtrationwere filtered
  4. concentrationthe filtrate was concentrated
  5. custompurified by silica gel chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-1eb5227f09714bf694a6502589d08207
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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