Hydrogen Cyanide → 5-Methyl-5-phenethyl-imidazolidine-2,4-dione

HRID 1614010Notes

Reaction equation

HRID 1614010 reaction equation
[C:1](=[O:4])([O-])[O-].[NH4+:5].[NH4+:6].C#N.[C:9]1([CH2:15][CH2:16][CH:17](O)[CH3:18])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:20][OH:21].O>>[CH3:18][C:17]1([CH2:16][CH2:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:6][C:20](=[O:21])[NH:5][C:1]1=[O:4]

Participants

5

Reactant 4

HCID 768Hydrogen CyanideHCID 613024-Phenyl-2-butanolHCID 517111Ammonium CarbonateHCID 22242641Methanol--water (1/1)

Product 1

HCID 2323175-Methyl-5-phenethyl-imidazolidine-2,4-dione

Conditions

Temperature
40 °C

Procedure

A suspension of 144.1 g (1.5 Mol) ammonium carbonate in 800 ml methanol/water 1:1 mixture is prepared in a 2 liter three-necked flask. At a temperature of 20° C. 43.2 ml (1.1 Mol) hydrocyanic acid are added within 1 minute. 152.8 g (1.0 Mol) 4-phenyl-2-butanol (benzyl acetone) are then added dropwise, leading to a slight exothermic reaction (temperature increase to ca. 30° C.). The white emulsion is maintained at 40° C. for 1 hour and then for 2.5 hours at 60° C. The precipitate is suction filtered, washed twice with 50 ml methanol/H2O 1:1 and dried in a vacuum at 60° C.

Workup

  1. customis prepared in a 2 liter three-necked flask
  2. customAt a temperature of 20° C
  3. customleading to a slight exothermic reaction (temperature increase to ca. 30° C.)
  4. filtrationfiltered
  5. washwashed twice with 50 ml methanol/H2O 1:1
  6. customdried in a vacuum at 60° C.

Sources & evidence

ORD record
ord-3b3d7d5290254e57b18887f0cceec989
Source dataset
uspto-grants-1993_03
Patent number
US05194644

Reaction notes

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