HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 3-(2-Naphthylcarbonyl)-5,5-diphenylimidazolidine-2,4-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 5,5-Diphenylhydantoin | HCID 1775 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-Naphthoyl chloride | HCID 75246 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-(2-Naphthylcarbonyl)-5,5-diphenylimidazolidine-2,4-dione | HCID 9801442 | 54.7% |
Reaction Steps
0.5 g of 5,5-diphenylimidazolidine-2,4-dione was dissolved in tetrahydrofuran (5 mL), and sodium hydride (60%, in oil) (87 mg) was added at 0° C. under ice-cooling. After stirred for 30 minutes, 2-naphthoyl chloride (415 mg) was added at 0° C., followed by stirring at room temperature for 2.5 hours. After water was carefully added, ethyl acetate (200 mL) was added, and the layers were separated. The resulting organic layer was washed with a saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was distilled off. Further purification by silica gel chromatography (hexane:ethyl acetate=3:1) afforded white crystals. The resulting fraction was recrystallized from isopropyl ether (IPE) to obtain 441 mg of white crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06919365B2 |
| Source dataset | uspto-grants-2005_07 |
| ORD ID | ord-2dd12f52a86747dbad6fa52122749330 |
| Source note | uspto-grants-2005_07 |