Phenacyl bromide → HCID 69733102, compound

HRID 896594Notes

Reaction equation

HRID 896594 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.Br[CH2:33][C:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:35].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[C:1]1([C:11]([N:13]2[C:17](=[O:18])[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:15]([CH2:33][C:34](=[O:35])[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[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

Participants

6

Reactant 4

HCID 6259Phenacyl bromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 12112009HCID 12112009, compound

Product 1

HCID 69733102HCID 69733102, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Naphthylcarbonyl-5,5-diphenylimidazolidine-2,4-dione (100 mg) was dissolved in DMF (2 mL), 2-bromoacetophenone (52 mg) was added, and potassium carbonate (36 mg) was further added. The reaction solution was stirred at room temperature overnight. Ethyl acetate (100 mL) was added to the reaction solution, and the solution was washed with 1N hydrochloric acid, an aqueous saturated sodium bicarbonate solution and a saturated brine in turn. After the solution was dried over anhydrous magnesium sulfate, the solvent was distilled off. The resulting residue was recrystallized from IPE to obtain 69 mg of white crystals.

Workup

  1. washthe solution was washed with 1N hydrochloric acid
  2. dry with materialAfter the solution was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customThe resulting residue was recrystallized from IPE

Sources & evidence

ORD record
ord-b4c9dc6f587849bd94c8b3383affcd2e
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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