Ethyl Acetate → 5,5-Dimethyl-3-naphthylcarbonylimidazolidine-2,4-dione

HRID 896582Notes

Reaction equation

HRID 896582 reaction equation
[K].[CH3:2][C:3]1([CH3:10])[NH:7][C:6](=[O:8])[NH:5][C:4]1=[O:9].[C:11]1([C:21](Cl)=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.C(OCC)(=O)C>O1CCCC1>[CH3:2][C:3]1([CH3:10])[NH:7][C:6](=[O:8])[N:5]([C:21]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[O:22])[C:4]1=[O:9]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 701461-Naphthalenecarbonyl chlorideHCID 697307535,5-Dimethylimidazolidine-2,4-dione potassium salt

Product 1

HCID 121120155,5-Dimethyl-3-naphthylcarbonylimidazolidine-2,4-dioneYield 31.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5,5-Dimethylimidazolidine-2,4-dione potassium salt (1.47 g) was suspended in tetrahydrofuran (5 mL), 1-naphthoyl chloride (1.46 g) was added, and the mixture was stirred at room temperature overnight. Ethyl acetate (50 mL) was added to the reaction solution, and the mixture was filtered with a membrane filter (0.25 μm). The resulting organic layer was purified by silica gel chromatography (hexane:ethyl acetate=1:1) to obtain 674 mg of white crystals.

Workup

  1. filtrationthe mixture was filtered with a membrane
  2. filtrationfilter (0.25 μm)
  3. customThe resulting organic layer was purified by silica gel chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-b2fdc98f3cdb46f598f647b25bdf153c
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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