Hydantoin → 5-(4-Methyl-4-nitropentylidene)hydantoin

HRID 1744030Notes

Reaction equation

HRID 1744030 reaction equation
[CH3:1][C:2]([N+:8]([O-:10])=[O:9])([CH3:7])[CH2:3][CH2:4][CH:5]=O.[NH:11]1[CH2:17][C:15](=[O:16])[NH:14][C:12]1=[O:13].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH3:1][C:2]([N+:8]([O-:10])=[O:9])([CH3:7])[CH2:3][CH2:4][CH:5]=[C:17]1[NH:11][C:12](=[O:13])[NH:14][C:15]1=[O:16]

Participants

5

Reactant 3

HCID 10006HydantoinHCID 10340Sodium CarbonateHCID 122640094-Methyl-4-nitrovaleraldehyde

Product 1

HCID 695837495-(4-Methyl-4-nitropentylidene)hydantoinYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Oily 4-methyl-4-nitropentanal (4.0 g, 28 mmol), hydantoin (4.0 g, 40 mmol) and sodium carbonate (2.8 g, 20 mmol) were added to 50% aqueous acetonitrile (200 ml) and the mixture was refluxed with stirring for 3 days. The reaction mixture was concentrated and extracted three times with ethyl acetate. The organic layer was concentrated to dryness to give 5-(4-methyl-4-nitropentylidene)hydantoin (3.15 g, 13.9 mmol, yield 50.0%).

Workup

  1. temperaturethe mixture was refluxed
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted three times with ethyl acetate
  4. concentrationThe organic layer was concentrated to dryness

Sources & evidence

ORD record
ord-c01c41f69f9a410283dda1b0d2b7ddfd
Source dataset
uspto-grants-2006_03
Patent number
US07012152B2

Reaction notes

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