Water → 4-{N-[1H-imidazol-1-yl]-N-[(6-methoxy-benzothien-3-yl)methyl]amino}benzonitrile

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Reaction Steps

3-Chloromethyl-6-methoxy-benzothiophene (12.35 g, 58.06 mmol) was added to a mixture of 4[N-(1H-imidazol-1-yl)amino]benzonitrile (9.72 g, 52.78 mmol), K2CO3 (14.60 g, 105.56 mmol) and potassium iodide (0.10 g, 0.60 mmol) in dry DMF (70 ml) at room temperature. The mixture was then stirred at room temperature overnight and after poured into water and extracted with ethyl acetate, dried over Na2SO4, filtered, and concentrated under vacuum to give the crude product as solid (14.30 g). Flash chromatography on silica gel (toluene/dioxan: 6/4) yielded the expected product (10.50 g, 55%, powder).

Provenance & Evidence