反应 #79145

反应方程式

(E)-cinnamoyl chloride

N-(3-pyridyl)-o-phenylenediamine

→

brown solids

收率 34.0%

(E)-1-(3-Pyridyl)-2-styryl-1H-benzimidazole

收率 34.0%

溶剂

xylene

反应条件

后处理

1. 1
   温度the resulting mixture was heated
2. 2
   温度to reflux
3. 3
   其他removing water using a Dean-Stark apparatus for 11 h
4. 4
   温度After cooling
5. 5
   浓缩the reaction mixture was concentrated to dryness
6. 6
   workup.DISSOLUTIONThe residue was dissolved into ethyl acetate (100 ml)
7. 7
   洗涤washed consecutively with saturated aqueous sodium bicarbonate solution (50 ml) and brine (50 ml)
8. 8
   干燥dried (magnesium sulfate)
9. 9
   浓缩concentrated to dryness
10. 10
    其他The residue was purified by column chromatography (silica gel, 165 g; n-hexane/ethyl acetate (3/2 to 1/1))

实验过程

To a stirred suspension of N-(3-pyridyl)-o-phenylenediamine (0.93 g, 5 mmol; Kirsch, P.; Schoenleben-Janas, A.; Schirmer, R. H. Liebigs Ann. Org. Bioorg. Chem., 1995, 7, 1275) in xylene (60 ml) was added (E)-cinnamoyl chloride (0.83 g, 5 mmol). After stirring at the room temperature for 1h, the resulting mixture was heated to reflux removing water using a Dean-Stark apparatus for 11 h. After cooling, the reaction mixture was concentrated to dryness. The residue was dissolved into ethyl acetate (100 ml), washed consecutively with saturated aqueous sodium bicarbonate solution (50 ml) and brine (50 ml), dried (magnesium sulfate) and concentrated to dryness. The residue was purified by column chromatography (silica gel, 165 g; n-hexane/ethyl acetate (3/2 to 1/1)) to give 0.77 g (34%) of brown solids. Recrystallization from isopropyl ether yielded 0.50 g of the titled compound as pink solids. MW: 297.36; mp: 118.0-118.5° C.; 1H-NMR (CDCl3) δ: 8.84 (1H, dd, J=4.8, 1.5 Hz), 8.79 (1H, d, J=2.6 Hz), 8.00 (1H, d, J=15.8 Hz), 7.88-7.79 (2H, m), 7.61 (1H dd, J=8.1, 4.8 Hz), 7.50-7.44 (2H, m), 7.39-7.15 (6H, m), 6.78 (1H, d, J=15.8 Hz).

来源