1,3-Diazaspiro[4.5]decane-2,4-dione → HCID 22351158, compound

HRID 896606Notes

Reaction equation

HRID 896606 reaction equation
[CH2:1]1[CH2:6][CH2:5][C:4]2([NH:12][C:10](=[O:11])[NH:9][C:7]2=[O:8])[CH2:3][CH2:2]1.[H-].[Na+].[C:15]1([C:25](Cl)=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1>O1CCCC1>[C:15]1([C:25]([N:9]2[C:7](=[O:8])[C:4]3([CH2:3][CH2:2][CH2:1][CH2:6][CH2:5]3)[NH:12][C:10]2=[O:11])=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 127991,3-Diazaspiro[4.5]decane-2,4-dioneHCID 24758Sodium hydrideHCID 701461-Naphthalenecarbonyl chloride

Product 1

HCID 22351158HCID 22351158, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5,5-Pentamethylenehydantoin (2.00 g) was dissolved in tetrahydrofuran (10 mL), and sodium hydride (60%, in oil) (0.49 g) was added at 0° C. under ice-cooling. After stirred for 30 minutes, 1-naphthoyl chloride (2.33 g) was added at 0° C., and the mixture was stirred at room temperature overnight. After the solvent was distilled off, ethyl acetate (100 mL) was added to the reaction solution, and the solution was washed with 1N hydrochloric acid, an aqueous saturated sodium bicarbonate solution and a saturated brine in turn. After drying over anhydrous magnesium sulfate, the solvent was distilled off to obtain the white solid. Further recrystallization with IPE and ethyl acetate afforded 1.87 g of white crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature overnight
  3. distillationAfter the solvent was distilled off
  4. additionethyl acetate (100 mL) was added to the reaction solution
  5. washthe solution was washed with 1N hydrochloric acid
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customto obtain the white solid
  9. customFurther recrystallization with IPE and ethyl acetate

Sources & evidence

ORD record
ord-32fdaca3e49f466ab77ba57075de0ee1
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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