Ethyl isocyanate → Methyl 5-bromo-2-(3-ethylureido)isonicotinate
Reaktionsgleichung
[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]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 40 °C
Versuchsvorschrift
Methyl 2-amino-5-bromoisonicotinate (200 g, 865 mmol) was dissolved in chloroform (1.2 L) and placed into a 2 L Parr apparatus. Ethyl isocyanate (204 mL, 2.59 mol) was added, and the Parr apparatus was heated at 40° C. for 36 h at which time the reaction was determined to be complete. The mixture was then cooled to room temperature, concentrated, and the solid was dissolved in 2:1 ethyl acetate: tetrahydrofuran (3 L). This solution was extracted with water (1 L), and the water was back extracted with ethyl acetate (300 mL). The organic layers were combined then dried over sodium sulfate, filtered, and concentrated yielding 261 g (quant) of methyl 5-bromo-2-(3-ethylureido)isonicotinate as a dark yellow solid.
Aufarbeitung
- temperatureThe mixture was then cooled to room temperature
- concentrationconcentrated
- dissolutionthe solid was dissolved in 2:1 ethyl acetate
- extractionThis solution was extracted with water (1 L)
- extractionthe water was back extracted with ethyl acetate (300 mL)
- dry with materialThe organic layers were combined then dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-5d2a52f3cd224c85931abee710a0e525
- Quelldatensatz
- uspto-grants-2013_10
- Patentnummer
- US08569484B2
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