Reaktionsgleichung
C(O[CH:4](OCC)[C:5](=[NH:15])[NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=1)C>S(=O)(=O)(O)O>[F:14][C:10]1[CH:9]=[C:8]2[C:13]([CH:4]=[C:5]([NH2:15])[N:6]=[CH:7]2)=[CH:12][CH:11]=1Komponenten
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
The crude 2,2-diethoxy-N-(3-fluorobenzyl)acetimidamide (22 g) was added dropwise to conc. sulfuric acid (200 mL) at 20˜25° C. with stirring. The mixture was stirred at room temperature for 48 hours. Then this mixture was quenched with ice (1 Kg), and a 12 N NaOH solution (400 mL) was added. The final pH of 9˜10 was reached. The suspension was extracted with CH2Cl2 (5×2 L). The organic layers were combined, washed with brine (500 mL), dried over anhydrous Na2SO4, filtered and concentrated to dryness. The crude material was purified by silica gel chromatography (EtOAc/Hexane=1/1) and afforded the title compound (330 mg, 2.5% yield based on m-fluorobenzylamine) as a yellow solid. 1H NMR (300 MHz, CDCl3): 9.17 (s, 1H), 8.66 (s, 1H), 8.01˜8.07 (m, 2H), 7.68 (dd, J=2.4, and 8.7 Hz, 1H), 7.58 (m, 1H); MS: m/z 163.1 (M+H+).
Aufarbeitung
- stirringThe mixture was stirred at room temperature for 48 hours
- customThen this mixture was quenched with ice (1 Kg)
- additiona 12 N NaOH solution (400 mL) was added
- extractionThe suspension was extracted with CH2Cl2 (5×2 L)
- washwashed with brine (500 mL)
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated to dryness
- customThe crude material was purified by silica gel chromatography (EtOAc/Hexane=1/1)
Quellen und Nachweise
- ORD-Eintrag
- ord-4a9083c6b428441393955558a80cce26
- Quelldatensatz
- uspto-grants-2013_06
- Patentnummer
- US08461339B2
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