Benzyl Bromide → HCID 12112016, compound

HRID 896593Notes

Reaction equation

HRID 896593 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.[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[CH2:32]([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])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 12112009HCID 12112009, compound

Product 1

HCID 12112016HCID 12112016, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Naphthylcarbonyl-5,5-diphenylimidazolidine-2,4-dione (200 mg) was dissolved in DMF (2 mL), benzyl bromide (45 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, and the solvent was distilled off. The resulting residue was recrystallized from IPE to obtain 55 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-900b1d8c9f27453481c4afeb938f7e61
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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