Urea → BARBITURIC ACID, 5-IPR

HRID 1281084Notes

Reaction equation

HRID 1281084 reaction equation
[CH:1]([CH:4]([C:10]([O:12]CC)=O)[C:5]([O:7]CC)=O)([CH3:3])[CH3:2].C[O-].[Na+].[NH2:18][C:19]([NH2:21])=[O:20]>CO>[CH3:3][CH:1]([CH:4]1[C:5](=[O:7])[NH:21][C:19](=[O:20])[NH:18][C:10]1=[O:12])[CH3:2]

Participants

5

Reactant 3

HCID 1176UreaHCID 12966Diethyl isopropylmalonateHCID 10942334Sodium Methoxide

Product 1

HCID 81874BARBITURIC ACID, 5-IPRYield 69.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

456 g (2.25 mol) of diethyl isopropylmalonate, 650 ml of a 30% methanolic sodium methoxide solution and 910 ml of methanol are charged to a 2 liter reactor equipped with an anchor stirrer. The mixture is brought to reflux for thirty minutes before adding 135 g (2.25 mol) of urea in the solid form while maintaining the reflux. The reaction mixture at the end of the reaction is a thick white suspension which is brought to dryness by evaporation of the methanol under vacuum. The residue is taken up in 1370 ml of water and then filtered after cooling to 20° C. The filtrate is treated by addition of the amount of hydrochloric acid needed to bring the pH to 2-3, and the precipitate obtained is filtered off under cold conditions and washed with ice-cold water in order to obtain 267 g of 5-(1-methylethyl)pyrimidine-2,4,6(1H,3H,5H)-trione.

Workup

  1. customequipped with an anchor stirrer
  2. temperatureto reflux for thirty minutes
  3. temperaturewhile maintaining the reflux
  4. customis brought to dryness by evaporation of the methanol under vacuum
  5. filtrationfiltered
  6. additionThe filtrate is treated by addition of the amount of hydrochloric acid
  7. customthe precipitate obtained
  8. filtrationis filtered off under cold conditions
  9. washwashed with ice-cold water in order

Sources & evidence

ORD record
ord-09785d7a12f045d1b73381a2b99553c0
Source dataset
uspto-grants-2002_09
Patent number
US06452006B1

Reaction notes

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