反応 #79145

反応方程式

(E)-cinnamoyl chloride

N-(3-pyridyl)-o-phenylenediamine

→

brown solids

収率 34.0%

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

収率 34.0%

溶媒

xylene

反応条件

後処理

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

実験手順

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).

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