Malonic Acid → 1,3-diphenyl-2,4,6(1H,3H,5H)-pyrimidinetrione

HRID 75635

Reaction equation

HRID 75635 reaction equation
[C:1]1([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17](O)(=[O:22])[CH2:18][C:19](O)=[O:20]>C(OC(=O)C)(=O)C>[C:11]1([N:10]2[C:19](=[O:20])[CH2:18][C:17](=[O:22])[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]2=[O:9])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 867Malonic AcidHCID 7595Carbanilide

Product 1

HCID 27849521,3-diphenyl-2,4,6(1H,3H,5H)-pyrimidinetrioneYield 40%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
90 °C

Procedure

Acetic anhydride (290 ml) was added to 1,3-diphenylurea 18 (148 g), malonic acid 4 (81.6 g) was added under a nitrogen atmosphere, and the mixture was stirred at 90° C. for 3 hrs. The mixture was stirred at 100° C. for 1.5 hrs and allowed to cool to room temperature. The reaction mixture was concentrated under reduced pressure. Ethanol (500 ml) was added to the residue, and the mixture was stirred at 90° C. When the mixture was cooled to 40° C., the crystals were collected by filtration, washed with ethanol and dried to give 1,3-diphenyl-pyrimidine-2,4,6-trione 19 (78.0 g, yield 40%).

Workup

  1. additionwas added under a nitrogen atmosphere
  2. stirringThe mixture was stirred at 100° C. for 1.5 hrs
  3. temperatureto cool to room temperature
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additionEthanol (500 ml) was added to the residue
  6. stirringthe mixture was stirred at 90° C
  7. temperatureWhen the mixture was cooled to 40° C.
  8. filtrationthe crystals were collected by filtration
  9. washwashed with ethanol
  10. customdried

Sources & evidence

ORD record
ord-5bc2ea202f5a4324ab8f4d8de557b541
Source dataset
uspto-grants-2014_09
Patent number
US08835443B2

Linked notes

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