Ethanol → 5-(neo-Pentyl)hydantoin

HRID 431279Notes

Reaction equation

HRID 431279 reaction equation
[C-]#N.[Na+].[CH2:4]([CH:6]([CH2:9][CH3:10])[CH:7]=O)[CH3:5].[C:11](=[O:14])([O-])[O-].[NH4+:15].[NH4+:16].[CH2:17]([OH:19])C>O>[CH2:4]([CH:6]([CH:7]1[NH:16][C:17](=[O:19])[NH:15][C:11]1=[O:14])[CH2:9][CH3:10])[CH3:5]

Participants

6

Reactant 4

HCID 702EthanolHCID 73592-EthylbutyraldehydeHCID 8929Sodium CyanideHCID 517111Ammonium Carbonate

Product 1

HCID 114351875-(neo-Pentyl)hydantoinYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Sodium cyanide (12.0 g, 244.8 mmol) and 2-ethylbutyraldehyde (10.0 mL, 81.3 mmol) were added to ammonium carbonate (25.4 g, 325.3 mmol) in H2O (300 mL). Ethanol (300 mL) was added and salts precipitated. The reaction mixture was heated to 90° C. After 1 h, the mixture became homogeneous and was stirred at 90° C. for 18 h. After cooling to 25° C., about 500 mL of solvent was removed in vacuo. Concentrated HCl was added to acidify the mixture to pH 1-2 and a precipitate formed. It was filtered and the precipitate was recrystallized from EtOAc to afford 5-(1-ethyl-propyl)-imidazolidine-2,4-dione as a white solid (12.9 g, 93%). Mass Spectrum (−ESI): 169 (M−H)−.

Workup

  1. customsalts precipitated
  2. temperatureAfter cooling to 25° C.
  3. customabout 500 mL of solvent was removed in vacuo
  4. additionConcentrated HCl was added
  5. customa precipitate formed
  6. filtrationIt was filtered
  7. customthe precipitate was recrystallized from EtOAc

Sources & evidence

ORD record
ord-f34a90feb53e4826ad556c9f79ae9f50
Source dataset
uspto-grants-2003_12
Patent number
US06657070B2

Reaction notes

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