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

HRID 1773330

Reaktionsgleichung

Reaktionsgleichung von HRID 1773330
[C:1]([OH:7])(=O)[CH2:2][C:3]([OH:5])=O.[CH3:8][NH:9][C:10]([NH2:12])=[O:11].C(OC(=O)C)(=O)C>C(O)(=O)C>[CH3:8][N:9]1[C:1](=[O:7])[CH2:2][C:3](=[O:5])[NH:12][C:10]1=[O:11]

Komponenten

5

Edukt 3

HCID 867Malonic AcidHCID 7918Acetic AnhydrideHCID 11719Methylurea

Produkt 1

HCID 757221-Methyl-2,4,6(1H,3H,5H)-pyrimidinetrioneAusbeute 65,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of malonic acid (80 g, 0.79 mol) and methylurea (50 g, 0.68 mol) in 180 ml of acetic acid at 70° C., acetic anhydride (130 ml, 1.37 mol) is added slowly. After the completion of the addition, the reaction mixture is stirred at 90° C. for 3 hours, and then cooled to room temperature. The solvent is removed under reduced pressure, and the residue is treated with 350 mL of ethanol to precipitate out yellowish solid. The solid is recrystallized from ethanol to give 63.1 g product as crystalline solids (Yield: 65.8%). m.p.=131.2-133.1° C. [Lit.1: m.p.=130-131.5° C.].

Aufarbeitung

  1. additionAfter the completion of the addition
  2. temperaturecooled to room temperature
  3. customThe solvent is removed under reduced pressure
  4. additionthe residue is treated with 350 mL of ethanol
  5. customto precipitate out yellowish solid
  6. customThe solid is recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-adaeeff308604d0d918dbb9e53220d66
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255099B2

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