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Water → HCID 12112009, compound

HRID 896577
Notes
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Reaction equation

HRID 896577 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:22]1([C:32](Cl)=[O:33])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1.O>O1CCCC1.C(OCC)(=O)C>[C:22]1([C:32]([N:9]2[C:8](=[O:13])[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:11][C:10]2=[O:12])=[O:33])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 1775PhenytoinHCID 24758Sodium hydrideHCID 701461-Naphthalenecarbonyl chloride

Product 1

HCID 12112009HCID 12112009, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 8028Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

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, 1-naphthoyl chloride (396 mg) was added at 0° C., followed by stirring at room temperature for 2.5 hours. After water was added carefully, 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=7:3) afforded 544 mg of white powder.

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 2.5 hours
  3. customthe layers were separated
  4. washThe resulting organic layer was washed with a saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customFurther purification by silica gel chromatography (hexane: ethyl acetate=7:3)

Sources & evidence

ORD record
ord-1c7b54460c0c46c4afe379e51e20c38c
Source dataset
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06919365B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes