Ammonium Chloride → HCID 178519458, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of {[6-(3-benzoyl-1-benzofuran-2-yl)-1-bromo-2-naphthyl]oxy} acetonitrile (0.174 g, 0.361 mmol) in DMF (10 mL) at room temperature was added NaN3 (0.117 g, 1.81 mmol) followed by NH4Cl (0.097 g, 1.81 mmol). The reaction was heated to 100° C. for 2 h. After this time, it was concentrated and diluted with 2 N HCl (˜5 mL). This mixture was stirred at room temperature for 1 h. The solid was filtered and washed with excess water and hexane then dried under high vacuum to afford the product (0.190 g, 99%) as a light. brown solid, mp>183° C. (dec.). Mass spectrum (+APCl, [M+NH4]+) m/z 542. 1HNMR (500 MHz, DMSO-d6): δ14.75-17.75 (br s, 1H), 8.28 (d, 1H, J=2.0 Hz), 8.03 (d, 1H, J=9.0 Hz), 8.00 (d, 1H, J=8.8 Hz), 7.78-7.83 (m, 3H), 7.76 (dd, 1H, J=1.7, 8.8 Hz), 7.67 (d, 1H, J=9.0 Hz), 755 (d, J=7.6 Hz, 1H), 7.32-7.38 (m, 3H), 7.45-7.52 (m, 2H), and 5.71 ppm (s, 2H). Elemental analysis for C27H17BrN4O3.1.0H2O: Calculated: C, 59.68; H, 3.52; N, 10.31. Found: C, 59.72; H, 3.23; N, 10.51.

Provenance & Evidence