Water → HCID 49783911, compound

Participants

Reaction Steps

To an ice cold (0-5° C.) solution of ammonium hydroxide (160 mL) was added a solution of ethyl 3-[(dimethylamino)diazenyl]-5-phenylselenophene-2-carboxylate (1.2 g) in THF (25 mL) for 5 min and a catalytic amount of PEG-400 was added and stirred at rt for 48 h. The solution was poured into ice cooled water and extracted with chloroform (3×100 mL). The combined organic layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using chloroform-methanol (94:6) as eluents to give the product as off-white solid, which was recrystallized from chloroform-hexane (270 mg, 31%), mp 222-224° C. IR (Neat) νmax 3346, 2927, 2850, 1645, 1594, 1221, 1113, 1019, 875, 850 cm−1; 1H NMR (400 MHz, CDCl3): δ 8.25 (1H, s, —CONH2), 7.87 (1H, s, H-4), 7.57-7.60 (2H, m, Ar—H), 7.30-7.40 (3H, m, Ar—H), 6.18 (1H, br s, —CONH2), 3.58 (3H, s, —N—CH3), 3.19 (3H, s, —N—CH3); 13C NMR (100 MHz, DMSO-d6): δ 165.6, 152.1, 151.9, 136.1, 131.1, 128.9, 128.5, 126.2, 118.1, 43.7, 36.6; LC-MS (positive ion mode): m/z 343, 345 (M+Na)+.

Provenance & Evidence