Reaktion #79162

Reaktionsgleichung

oxalic acid

N-(2-pyridyl)-o-phenylenediamine

2-methoxycinnamoyl chloride

(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole

→

titled compound

(E)-2-Methoxystyryl-1-(2-pyridyl)-1H-benzimidazole oxalate

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenConcentration and recrystallization from ethyl acetate/n-hexane

Vorschrift

Free base of the titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine and 2-methoxycinnamoyl chloride (Vallaerda, J.; Appelberg, U.; Csoeregh, I.; Hacksell, U. J. Chem. Soc. Perkin Trans. I; 1994, 17, 461) according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base and oxalic acid were dissolved into ethyl acetate. Concentration and recrystallization from ethyl acetate/n-hexane yielded the titled compound. MW: 417.42; mp: 123.0-125.0° C.; 1H-NMR (DMSO) δ: 8.81-8.77 (1H, m), 8.20 (1H, td, J=7.7,2.0 Hz), 8.10 (1H, d, J=16.1 Hz), 7.75 (2H, dd, J=8.1, 1.1 Hz), 7.68-7.62 (1H, m), 7.57 (1H, dd, J=7.7, 1.5 Hz), 7.46-7.42 (1H, m), 7.39-7.23 (4H, m) 7.08 (1H, d, J=7.7 Hz), 6.97 (1H, t, J=7.3 Hz), 3.86 (3H, s).

Quelle