Phenacyl bromide → HCID 69732580, compound

HRID 896599Notes

Reaction equation

HRID 896599 reaction equation
[CH3:1][C:2]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[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[CH2:30][C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:32].C(OCC)(=O)C>CN(C=O)C>[CH3:1][C:2]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:6]([CH2:30][C:31](=[O:32])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=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 69732576HCID 69732576, compound

Product 1

HCID 69732580HCID 69732580, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Methyl-3-naphthylcarbonyl-5-phenylimidazolidine-2,4-dione (43 mg) was dissolved in DMF (0.4 mL), and sodium hydride (60%, in oil) (5 mg) was added. Then, 25 mg of 2-bromoacetophenone 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 33 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-a1d6bc3ffbbd4bd5a04ae0b6bc82c9d6
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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