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

HRID 257378

반응식

HRID 257378 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 154305Carbamic acid, (1,3-dioxo-1,3-propanediyl)bis-, diethyl ester수율 43.1%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-71ec91ca29024755b381ceb386a9c563
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05262390

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