Malonic Acid → Carbamic acid, (1,3-dioxo-1,3-propanediyl)bis-, diethyl ester

HRID 257378

Reaktionsgleichung

Reaktionsgleichung von HRID 257378
[C:1]([OH:7])(=O)[CH2:2][C:3]([OH:5])=O.[C:8](=[O:13])([O:10][CH2:11][CH3:12])[NH2:9].P(Cl)(Cl)(Cl)=O>O>[C:3]([NH:9][C:8]([O:10][CH2:11][CH3:12])=[O:13])(=[O:5])[CH2:2][C:1]([NH:9][C:8]([O:10][CH2:11][CH3:12])=[O:13])=[O:7]

Komponenten

5

Edukt 3

HCID 867Malonic AcidHCID 5641Carbamic acid, ethyl esterHCID 24813Phosphorus oxychloride

Produkt 1

HCID 154305Carbamic acid, (1,3-dioxo-1,3-propanediyl)bis-, diethyl esterAusbeute 43,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

With a mortar and pestle 10.40 g (0.100 mole) of malonic acid and 18.00 g (0.210 mole) of ethyl carbamate were ground to a fine powder. This powder was placed in a flask, and 16.0 mL (0.167 mole) of phosphorus oxychloride was added. This mixture was heated at 80° C. until the evolution of gas ceased. After this reaction mixture had cooled to ambient temperature, 210 mL of water was added. When the stiff glassy mixture became fluid, it was extracted with ethyl acetate. The combined extracts were washed in succession with saturated aqueous solutions of sodium bicarbonate and sodium chloride and were then dried over anhydrous magnesium sulfate and filtered. The solution was filtered through a short column of silica gel, which was eluted with ethyl acetate. The solvent was then evaporated under reduced pressure, leaving a crystalline mass of malonyldiurethane weighing 10.62 g. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

  1. customThis powder was placed in a flask
  2. temperatureAfter this reaction mixture had cooled to ambient temperature
  3. extractionwas extracted with ethyl acetate
  4. washThe combined extracts were washed in succession with saturated aqueous solutions of sodium bicarbonate and sodium chloride
  5. dry with materialwere then dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. filtrationThe solution was filtered through a short column of silica gel, which
  8. washwas eluted with ethyl acetate
  9. customThe solvent was then evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-71ec91ca29024755b381ceb386a9c563
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05262390

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