Reaction #487573

ord-10417475da6d40dbb7657d2781a3f4df

Reaction equation

O=P(Cl)(Cl)Cl
phosphoryl chloride
CN(C)C=O
DMF
O=C1CC(=O)NC(=O)N1
barbituric acid
→
O=CC1C(=O)NC(=O)NC1=O
2,4,6-trioxohexahydropyrimidine-5-carbaldehyde

Reactants

O=P(Cl)(Cl)Cl
phosphoryl chloride
CN(C)C=O
DMF
O=C1CC(=O)NC(=O)N1
barbituric acid
—
ice water

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturecooling
  2. 2
    TemperatureThe mixture is cooled
  3. 3
    Otherthe precipitate is separated off
  4. 4
    Washrinsed with water
  5. 5
    Otherdried at 45°
  6. 6
    Othergiving 2.5 g of “1”

Procedure

9.03 ml of phosphoryl chloride are added dropwise to 2 ml of dry DMF with ice-cooling. 1.5 g of barbituric acid are subsequently added, and the mixture is stirred at 100° for 4 h. The mixture is cooled, poured into ice-water, the precipitate is separated off, rinsed with water and dried at 45°, giving 2.5 g of “1”.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08741896B2uspto-grants-2014_06