Ethanol → 3-[2,5-Dioxo-4-[(2-propenyloxy)methyl]imidazolidin-4-yl]benzonitrile

HRID 2427148Notes

Reaction equation

HRID 2427148 reaction equation
[CH2:1]([O:4][CH2:5][C:6]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1C#N)=O)[CH:2]=[CH2:3].O.[C-:17]#[N:18].[K+].[C:20](=[O:23])([O-])[O-].[NH4+:24].[NH4+:25].C[CH2:27][OH:28]>>[O:28]=[C:27]1[NH:25][C:6]([C:8]2[CH:9]=[C:12]([CH:13]=[CH:14][CH:15]=2)[C:17]#[N:18])([CH2:5][O:4][CH2:1][CH:2]=[CH2:3])[C:20](=[O:23])[NH:24]1

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 86641460(2-(2-Propenyloxy)acetyl]benzonitrile

Product 1

HCID 671310093-[2,5-Dioxo-4-[(2-propenyloxy)methyl]imidazolidin-4-yl]benzonitrile

Conditions

Temperature
55 °C

Procedure

To a solution of 450 mg of 3-[(2-(2-propenyloxy)acetyl]benzonitrile (in EtOH (5 mL) and water (5 mL) 291 mg of potassium cyanide and ammonium carbonate are added. The mixture is refluxed one night at 55° C. The mixture is extracted with ethyl acetate, dried over magnesium sulfate and concentrated under vacuum to give the desired compound.

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6a5bfc1d08ce4aa281846337c9f5e2d7
Source dataset
uspto-grants-2011_06
Patent number
US07968581B2

Reaction notes

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