Water → HCID 12112011, compound

HRID 896579Notes

Reaction equation

HRID 896579 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]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(OCC)(=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:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[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

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 12112009HCID 12112009, compound

Product 1

HCID 12112011HCID 12112011, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Naphthylcarbonyl-5,5-diphenylimidazolidine-2,4-dione (879 mg) was dissolved in DMF (3 mL), tert-butyl bromoacetate (421 mg) was added, and potassium carbonate (299 mg) was further added. The reaction solution was stirred at room temperature overnight. After water was carefully added, ethyl acetate (200 mL) was added, followed by extraction. The resulting organic layer was washed with a saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was distilled off. Further, recrystallization from methanol afforded 846 mg of white crystals.

Workup

  1. extractionfollowed by extraction
  2. washThe resulting organic layer was washed with a saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customFurther, recrystallization from methanol

Sources & evidence

ORD record
ord-cd54ede4f8b14b9680b0d0b7af4a5707
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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