Ethyl Acetate → HCID 86592780, compound

HRID 896581Notes

Reaction equation

HRID 896581 reaction equation
[K].C[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:7][C:6](=[O:8])[NH:5][C:4]1=[O:9].[C:16]1([C:26](Cl)=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.[C:29](OCC)(=O)C>O1CCCC1>[CH3:29][N:7]1[CH:3]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:4](=[O:9])[N:5]([C:26]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[O:27])[C:6]1=[O:8]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 701461-Naphthalenecarbonyl chlorideHCID 69732011HCID 69732011, compound

Product 1

HCID 86592780HCID 86592780, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Methyl-5-phenylimidazolidine-2,4-dione potassium salt (228 mg) was suspended in tetrahydrofuran (5 mL), 1-naphthoyl chloride (188 mg) was added, and the mixture was stirred at room temperature overnight. To the reaction solution was added ethyl acetate (20 mL), and the mixture was filtered with a membrane filter (0.25 μm). After the solvent was distilled off, 364 mg of the resulting organic layer was purified by silica gel chromatography (hexane:ethyl acetate=2:1). Further recrystallization from ethyl acetate/IPE afforded 134 mg of white crystals.

Workup

  1. filtrationthe mixture was filtered with a membrane
  2. filtrationfilter (0.25 μm)
  3. distillationAfter the solvent was distilled off
  4. custom364 mg of the resulting organic layer was purified by silica gel chromatography (hexane:ethyl acetate=2:1)
  5. customFurther recrystallization from ethyl acetate/IPE

Sources & evidence

ORD record
ord-43b3ae9801f849ce8ed2f974dfecca0e
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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