Ethyl Acetate → HCID 69732664, compound

HRID 896604Notes

Reaction equation

HRID 896604 reaction equation
[CH3:1][C:2]1([CH3:21])[NH:6][C:5](=[O:7])[N:4]([C:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)=[O:9])[C:3]1=[O:20].[H-].[Na+].[CH3:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([CH2:33]Br)=[O:32])=[CH:27][CH:26]=1.C(OCC)(=O)C>CN(C=O)C>[CH3:1][C:2]1([CH3:21])[N:6]([CH2:33][C:31](=[O:32])[C:28]2[CH:29]=[CH:30][C:25]([CH3:24])=[CH:26][CH:27]=2)[C:5](=[O:7])[N:4]([C:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)=[O:9])[C:3]1=[O:20]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 692722-Bromo-4'-methylacetophenoneHCID 121120155,5-Dimethyl-3-naphthylcarbonylimidazolidine-2,4-dione

Product 1

HCID 69732664HCID 69732664, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5,5-Dimethyl-3-naphthylcarbonylimidazolidine-2,4-dione (35 mg) was dissolved in DMF (0.4 mL), and sodium hydride (60%, in oil) (5 mg) was added. Then, 2-bromo-4-methylacetophenone (27 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 12 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-aa420ecf234c4da8b86b2c007ce099c0
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

Loading…