Ethyl isocyanate → Methyl 5-bromo-2-(3-ethylureido)isonicotinate

HRID 2061843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2061843
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([Br:12])=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH2:13]([N:15]=[C:16]=[O:17])[CH3:14]>C(Cl)(Cl)Cl>[Br:12][C:9]1[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]([NH:1][C:16]([NH:15][CH2:13][CH3:14])=[O:17])=[N:11][CH:10]=1

Komponenten

4

Edukt 2

HCID 8022Ethyl isocyanateHCID 25307230Methyl 2-amino-5-bromoisonicotinate

Produkt 1

HCID 59416007Methyl 5-bromo-2-(3-ethylureido)isonicotinateAusbeute 104,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A solution of methyl 2-amino-5-bromoisonicotinate (50 g, 216.5 mmol) in chloroform (500 mL) was placed into a sealed tube. Ethyl isocyanate (51 mL, 649.4 mmol) was then added in two parts over the course of 6 hours. The sealed tube was insulated and heated at 40° C. for 3 d. The reaction mixture was then cooled to room temperature, concentrated under reduced pressure, and extracted with ethyl acetate (3 L) and water (1 L). The ethyl acetate layer was then dried with sodium sulfate, filtered, and concentrated under reduced pressure to yield 68.4 g of a pale yellow solid (96%).

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with ethyl acetate (3 L) and water (1 L)
  4. dry with materialThe ethyl acetate layer was then dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8500ddfcbfb94a56a01f6f71dbe6fa35
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08283361B2

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