Ethyl Acetate → 1-(3-Chlorobenzyl)-5,5-dimethyl-3-naphthylcarbonylimidazolidine-2,4-dione

HRID 896601Notes

Reaction equation

HRID 896601 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+].[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28]Br.C(OCC)(=O)C>CN(C=O)C>[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28][N:6]1[C:2]([CH3:21])([CH3:1])[C:3](=[O:20])[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:5]1=[O:7]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 121120155,5-Dimethyl-3-naphthylcarbonylimidazolidine-2,4-dione

Product 1

HCID 121120171-(3-Chlorobenzyl)-5,5-dimethyl-3-naphthylcarbonylimidazolidine-2,4-dioneYield 27.8%

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, 3-chlorobenzyl bromide (26 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 14 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-9b758116e30a4d6dbaff90dd9a8e87bd
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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