Methyl iodide → 3-Methyl-6,7,8,9-tetrahydrobenzo[1,2-b]1, 2,3-triazino[4,5-d]selenophen-4-one

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Reaction Steps

To a solution of 6,7,8,9-tetrahydro-3H-benzo[1,2-b]1,2,3-triazino[4,5-d]selenophen-4-one (450 mg, 1.76 mmol) in acetone (50 mL) was added sequentially potassium carbonate (480 mg, 3.52 mmol), iodomethane (0.13 mL, 2.11 mmol) and a catalytic amount of PEG-400 was added and stirred at rt and the mixture was stirred at rt for 16 h. The solution was filtered and the solids were washed with acetone. Acetone was evaporated under reduced pressure and the residue was chromatographed over silica gel column using hexane-ethyl acetate (90:10) as eluents to give the product as a pale yellow color solid (340 mg, 72%), which was recrystallized from chloroform-hexane (170 mg), mp 110-112° C. IR (neat) νmax 3438, 1668, 1220, 1018 cm−1; 1H NMR (400 MHz, CDCl3): δ 4.05 (3H, s, —NCH3), 2.94-2.96 (4H, m, H-6,9), 1.91-1.97 (4H, m, H-7,8); 13C NMR (100 MHz, CDCl3): δ 156.1, 155.1, 152.5, 133.9, 128.5, 37.4, 28.4, 24.8, 23.6, 21.4; LC-MS (positive ion mode): m/z 268, 270 (M+H)+.

Provenance & Evidence