Ethanol → 5-Methyl-5-(3-methylphenyl)imidazolidine-2,4-dione

HRID 1245323Notes

Reaction equation

HRID 1245323 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH3:9])[CH:5]=[CH:6][CH:7]=1.[C-:11]#[N:12].[K+].[NH4+:14].[OH-:15].[OH2:16].[CH2:17](O)C>>[CH3:9][C:8]1([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)[NH:14][C:17](=[O:15])[NH:12][C:11]1=[O:16]

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 9032Potassium CyanideHCID 114553-MethylacetophenoneHCID 14923Ammonium Hydroxide

Product 1

HCID 219109805-Methyl-5-(3-methylphenyl)imidazolidine-2,4-dione

Conditions

Temperature
60 °C

Procedure

To a solution of 930 mg 3′-methylacetophenone in 5 mL anhydrous ethanol was added 2.04 g NH4HCO3, 542 mg KCN, then 2.1 mL conc. NH4OH. The mixture was stirred at 60° C. overnight. Addition of water and partial solvent removal induced crystallization. The product was vacuum filtered and washed several times with water. The resultant white solid was recrystallized from MeOH to yield 5-methyl-5-(3-methylphenyl)-imidazolidine-2,4-dione as a white solid. A solution of 351 mg of the imidazolidinedione product, 822 mg KMnO4 and 1.44 g NaOH in 20 mL H2O was heated to 95° C. for 2 hours, then allowed to cool to RT. Ethanol (5 mL) was added to decompose the remaining KMnO4, and the mixture filtered, acidified, and left to stand overnight. The fine precipitate that formed was recovered by gravity filtration to yield, after drying in vacuo, 5-methyl-5-(3-carboxyphenyl)-imidizalodine-2,4-dione as an off-white solid.

Workup

  1. customcrystallization
  2. filtrationfiltered
  3. washwashed several times with water
  4. customThe resultant white solid was recrystallized from MeOH

Sources & evidence

ORD record
ord-3fd70d292a2244deaaa2f12750e880c5
Source dataset
uspto-grants-2006_10
Patent number
US07125865B2

Reaction notes

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