Urea → 5-(4-methylphenyl)pyrimidine-2,4,6(1H,3H,5H)-trione

HRID 993068Notes

Reaction equation

HRID 993068 reaction equation
[Na].[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:15]([O:17]CC)=O)[C:10]([O:12]CC)=O)=[CH:5][CH:4]=1.[NH2:20][C:21]([NH2:23])=[O:22]>C(O)C>[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[C:10](=[O:12])[NH:23][C:21](=[O:22])[NH:20][C:15]2=[O:17])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 1176UreaHCID 570878Diethyl 2-(p-tolyl)malonateHCID 5360545Sodium

Product 1

HCID 45769115-(4-methylphenyl)pyrimidine-2,4,6(1H,3H,5H)-trione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of sodium (184 mg) in 12 ml of ethanol are added 0.95 ml of diethyl 2-(4-Methylphenyl)malonate and 360 mg of urea, then the mixture is refluxed for 3 hours. A white solid separates, which is filtered and redissolved in 4 ml of water. The solution is acidified to pH=1-2 by adding 6 N hydrochloric acid. A white solid separates, which is collected by filtration, washed with 15 ml of water and dried under vacuum. 619 mg of the product are obtained, m.p. 271° C.

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. filtrationA white solid separates, which is filtered
  3. dissolutionredissolved in 4 ml of water
  4. additionby adding 6 N hydrochloric acid
  5. filtrationA white solid separates, which is collected by filtration
  6. washwashed with 15 ml of water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-88f86ef24f0c4c0483d6ca9429ea7fdf
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

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