Hydrochloric Acid → HCID 49783915, compound

Participants

Reaction Steps

To a solution of ethyl 3-[(dimethylamino)diazenyl]-5-phenylselenophene-2-carboxylate (200 mg, 0.56 mmol) prepared as described in Example 3 step c) in methanol (5 mL) was added a solution of sodium hydroxide (113 mg, 2.84 mmol) in water (3 mL) and stirred at rt for 16 h. The mixture was diluted with ice cold water and acidified with dil. HCl. The mixture was stirred for 30 min and the precipitated solid was filtered, washed with water and dried. The product was recrystallized from hexane-chloroform to give the product as a brown color solid (100 mg, 54%), mp 212-214° C. IR (neat) νmax 3566, 2924, 1700, 1253, 1180, 1113, 1070, 1011, 838, 766 cm−; 1H NMR (400 MHz, CDCl3): δ 12.27 (1H, s, —COOH), 7.79 (1H, s, H-4), 7.55-7.57 (2H, m, Ar—H), 7.34-7.39 (3H, m, Ar—H), 3.65 (3H, s, —N—CH3), 3.25 (3H, s, —N—CH3); 13C NMR (100 MHz, CDCl3): δ 163.9, 155.2, 154.6, 135.5, 129.2, 129.1, 126.3, 124.9, 116.6, 44.4, 37.1; LC-MS (positive ion mode): m/z 346, 344 (M+Na)+.

Provenance & Evidence