Sodium Nitrite → HCID 136155074, compound

Participants

Reaction Conditions

Reaction Steps

To an ice cold (0° C.) solution of 3-aminobenzo[b]selenophene-2-carboxamide (1.0 g, 4.16 mmol) in concentrated sulfuric acid (25 mL) was added a cold (0° C.) solution of sodium nitrite (0.316 g, 4.58 mmol) in concentrated sulfuric acid (10 mL) for 10 min (while adding, the temperature should keep between −5-0° C.). After addition, the mixture was stirred at 0° C. for 1 h and at rt for 2 h. The reaction mixture was cooled, poured into crushed ice slowly with stirring for 15 min and stirred at the same temperature for 15 min. The solution was extracted with ethyl acetate (3×200 mL) and the combined EtOAc layer was washed with water, brine and dried over sodium sulfate. The solution was filtered, evaporated the solvent to give the product as a yellow color solid (200 mg, 19%), mp 176-178° C. 1H NMR (400 MHz, DMSO-d6): δ 15.48 (1H, s, —NH), 8.53-8.58 (1H, m, H-9), 8.41-8.46 (1H, m, H-6), 7.74-7.80 (2H, m, H-7,8).

Provenance & Evidence