1,2-Dibromoethane → 4-[(2-Bromo-ethyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

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Reaction Steps

Sodium hydride (240 mg, 6.0 mmol) was added to a solution of 4-([1,2,4]triazol-4-ylamino)-benzonitrile (926 mg, 5.0 mmol) in DMSO (25 ml) at r.t. The mixture was stirred for 1 hour at this temperature and 1,2-dibromethane (5 ml) was added. The reaction mixture was stirred overnight and ethyl acetate (100 ml) was added. The mixture was transferred into a separation funnel and extracted with water (twice 100 ml) and brine (20 ml). The organic layer was dried over sodium sulphate and concentrated under reduced pressure (water bath temperature <30° C.). The resulting orange oil was mixed with diethyl ether (100 ml) and filtered through a layer of silica (ca. 5 cm). The silica was washed with more diethyl ether (ca. 100 ml) to remove the excess of 1,2-dibromoethane; the crude product was washed from the silica with acetone (120 ml). The acetone solution was concentrated under reduced pressure and the residue was purified by column-chromatography (eluent: ethyl acetate) to give the title compound as a white solid. Yield: 628 mg (43%). 1H-NMR (400 MHz, d6-DMSO) δ=3.61 (t, J=6.2 Hz, 2H), 4.30 (t, J=6.4 Hz, 2H), 6.64 (d, J=9.0 Hz), 7.74 (d, 9.0 Hz, 2H), 8.97 (s, 2H). LRMS (FAB+):292.0 (100, [M+H]+)

Provenance & Evidence