Water → HCID 49783913, compound

Participants

Reaction Steps

To an ice cold (0-5° C.) solution of ammonium hydroxide (60 mL) was added a mixture of ethyl and methyl esters of 3-[(dimethylamino)diazenyl]-4,5,6,7-tetrahydrobenzo[2,1-d]selenophene-2-carboxylate (600 mg) in THF (6 mL) for 5 min. A catalytic amount of PEG-400 was added and stirred at rt for 66 h. The solution was poured into ice cooled water and extracted with chloroform (3×150 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 (98:2) as eluents to give the product as a pale brown color solid (100 mg, 18%), which was recrystallized from chloroform-hexane (70 mg), mp 198-202° C. IR (Neat) νmax 3347, 3163, 2932, 2860, 1631, 1342, 1313, 1220, 1103, 1020, 878 cm−1; 1H NMR (400 MHz, CDCl3): δ 8.21 (1H, s, —CONH2), 6.07 (1H, s, —CONH2), 3.51 (3H, br s, —NCH3), 3.14 (3H, br s, —NCH3), 2.80-2.82 (2H, m, H-4), 2.64-2.65 (2H, m, H-7), 1.72-1.80 (4H, m, H-5,6); 13C NMR (100 MHz, CDCl3): δ 165.9, 149.5, 145.9, 132.6, 129.5, 29.0, 28.6, 23.1, 22.7; LC-MS (positive ion mode): m/z 321, 323 (M+Na)+.

Provenance & Evidence