Malonic Acid → 1-Methyl-3-phenylpyrimidine-2,4,6(1H,3H,5H)-trione

HRID 986694Notes

Reaction equation

HRID 986694 reaction equation
C(OC(=O)C)(=O)C.[CH3:8][NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11].[C:19](O)(=[O:24])[CH2:20][C:21](O)=[O:22]>C(O)(=O)C>[CH3:8][N:9]1[C:21](=[O:22])[CH2:20][C:19](=[O:24])[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]1=[O:11]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 7918Acetic AnhydrideHCID 138801-Methyl-3-phenylurea

Product 1

HCID 155454941-Methyl-3-phenylpyrimidine-2,4,6(1H,3H,5H)-trione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

Acetic anhydride (16 ml, 0.17 mole) was added dropwise over three hours to a solution of 1-methyl-3-phenylurea (6 g, 0.04 mole) and malonic acid (4.6 g, 0.04 mole) in acetic acid (40 ml) at 60° C. After the addition was completed, the temperature was raised to 90° C. and maintained for four hours. The solvent was evaporated and the resulting residue treated with 0.1N NaOH (50 ml). After filtration, the solution was acidified with 0.2N HCl (120 ml). The solution was evaporated to dryness under reduced pressure, leaving solid 1-methyl-3-phenyl-2,4,6-(1H,3H,5H)- pyrimidinetrione upon cooling. It was recrystallized from ethanol to yield colorless crystals, m.p. 122.5°-123° C.

Workup

  1. additionAfter the addition
  2. temperaturemaintained for four hours
  3. customThe solvent was evaporated
  4. additionthe resulting residue treated with 0.1N NaOH (50 ml)
  5. filtrationAfter filtration
  6. customThe solution was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-81865963cd5e4e9680d97f40522854a3
Source dataset
uspto-grants-1987_12
Patent number
US04714838

Reaction notes

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