Ammonium Chloride → HCID 178446891, compound

Participants

Reaction Steps

Following the procedure described in Step 6 of Example 1, the title compound was prepared from 2-{[6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile (0.350 g, 0.913 mmol), sodium azide (0.297 g, 4.56 mmol), and ammonium chloride (0.246 g, 4.60) mmol) in DMF (6 mL). Crystallization from acetonitrile (also using charcoal), and drying of the product for 16 hours at 84° C. yielded a light yellow solid (0.0978 g), mp 150-151° C. Mass spectrum (+APCl, [M+H]+) m/z427; 1HNMR (400 MHz, DMSO-d6): δ16.8-17.1 (br, 1H), 8.4 (d, 1H, J=1.2 Hz), 8.0-8.05 (m, 3H), 7.85 (dd, 1H, J=8.5 Hz and 1.7 Hz), 7.7 (d, 1H, J=7.5 Hz), 7.65 (d, 1H, J=2.4 Hz) 7.45 (m, 3H), 5.65 (s, 2H), 2.75 (t, 2H, J=7.3 Hz), 1.5-1.6 (m, 2H), 1.1-1.2(m, 2H), and 0.7 ppm (t, 3H, J=7.4 Hz). Elemental Analysis for C25H22N4O3: Calculated: C, 70.41;H, 5.20; N, 13.14. Found: C, 70.21;H, 5.14; N, 13.23.

Provenance & Evidence