Reaktion #7185

Reaktionsgleichung

HCl

2-amino-3-methoxy-1-nitrobenzene

3-methoxy-1,2-phenylenediamine

2-amino-3-methoxy-nitrobenzene

chloroacetic acid

→

2-chloromethyl-4-methoxy-1H-benzimidazole

Ausbeute 86.6%

Lösungsmittel

MeOH

Reaktionsbedingungen

Vorschrift

A solution of 2-amino-3-methoxy-1-nitrobenzene (0.860 g, 5.11 mmol) in MeOH (50 mL) was hydrogenated (1 atm) over palladium, 10 wt. % on activated carbon (0.163 g). The resultant crude 3-methoxy-1,2-phenylenediamine was reacted with chloroacetic acid (0.953 g, 10.08 mmol) in refluxing 4 N HCl (10 mL) overnight. After aqueous workup, 0.87 g of 2-chloromethyl-4-methoxy-1H-benzimidazole was isolated as a red-brown solid, which was used without further purification.

Quelle