Synthesis and Characterization of 2-Selenobenzoic Acid Amide

To a suspension of 7 [52 (link)] (175 mg, 0.44 mmol) in dry toluene (3 mL), thionyl chloride (0.2 mL, 2.82 mmol) was added. The resulting mixture was refluxed until no gas evolution was observable and a clear solution was formed. The unreacted thionyl chloride was evaporated in vacuo and the residue was washed with dry toluene (three times, 2 mL each). The brown oil was solubilized in dry THF (8 mL) and poured into a 3 neck round bottom flask then pure ammonia was added until a precipitate was formed. The suspension was allowed to react at room temperature for 12 h. The solid was filtrated and the filtrate was evaporated in vacuo giving a yellow solid which was treated with Et₂O then filtered and recrystallized from EtOH giving the target compound as a white solid (120 mg; 71% yield). Mp = 221–223 °C; ¹H-NMR (DMSO-d₆) δ: 7.40 (t, J = 7.79 Hz, 1H, ArH); 7.60 (t, J = 8.29 Hz, 1H, ArH); 7.80 (dd, J = 0.72 and 7.77 Hz, 1H, ArH); 8.03 (d, J = 8.29 Hz, 1H, ArH); 9.18 (bs, 1H, NH) ppm; ¹³C-NMR (DMSO-d₆) δ: 125.77; 126.39; 127.40; 127.68; 131.70; 141.56; 168.89 ppm. ⁷⁷Se NMR (DMSO-d₆) δ: 796.71 ppm. HRMS calculated for [C₇H₆NOSe⁺] = 199.9615 found = 199.9621