Phenacyl bromide → HCID 69732068, compound

HRID 896603Notes

Reaction equation

HRID 896603 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+].Br[CH2:25][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27].C(OCC)(=O)C>CN(C=O)C>[CH3:1][C:2]1([CH3:21])[N:6]([CH2:25][C:26](=[O:27])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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 6259Phenacyl bromideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 121120155,5-Dimethyl-3-naphthylcarbonylimidazolidine-2,4-dione

Product 1

HCID 69732068HCID 69732068, compoundYield 14.1%

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-bromoacetophenone (25 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 7 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-5a6bffde14454b41a100a46908223fd0
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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