Malonic Acid → 1,3-Diethylbarbituric acid

HRID 986689Notes

Reaction equation

HRID 986689 reaction equation
C(OC(=O)C)(=O)C.[CH2:8]([NH:10][C:11]([NH:13][CH2:14][CH3:15])=[O:12])[CH3:9].[C:16]([OH:22])(=O)[CH2:17][C:18]([OH:20])=O>C(O)(=O)C>[CH2:8]([N:10]1[C:16](=[O:22])[CH2:17][C:18](=[O:20])[N:13]([CH2:14][CH3:15])[C:11]1=[O:12])[CH3:9]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 7918Acetic AnhydrideHCID 12194sym-Diethylurea

Product 1

HCID 1228891,3-Diethylbarbituric acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

Acetic anhydride (16 ml, 0.15 mole) was added dropwise over two hours to a solution of 1,3-diethylurea (5.3 g, 0.05 mole) and malonic acid (5.2 g, 0.05 mole) in acetic acid (40 ml) at 65° C. After the addition was complete, the temperature was raised to 90° C. and maintained there for three hours. The solvent was evaporated under reduced pressure and the residue boiled with ethanol for fifteen minutes. After some time, 1,3-diethyl-2,4,6-(1H,3H,5H)- pyrimidinetrione crystallized in cubic crystals, m.p. 52° C.

Workup

  1. additionAfter the addition
  2. temperaturemaintained there for three hours
  3. customThe solvent was evaporated under reduced pressure
  4. waitthe residue boiled with ethanol for fifteen minutes
  5. customAfter some time, 1,3-diethyl-2,4,6-(1H,3H,5H)- pyrimidinetrione crystallized in cubic crystals, m.p. 52° C.

Sources & evidence

ORD record
ord-190a7c8fc95144aa81910717e4971555
Source dataset
uspto-grants-1987_12
Patent number
US04714838

Reaction notes

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