Sodium Iodide → 3-{4-[(2-Aminoethyl)amino]-1,2,5-oxadiazol-3-yl}-4-[(4-bromo-2-furyl)methyl]-1,2,4-oxadiazol-5(4H)-one hydroiodide

Participants

Reaction Steps

To a solution of 3-{4-[(2-azidoethyl)amino]-1,2,5-oxadiazol-3-yl}-4-[(4-bromo-2-furyl)methyl]-1,2,4-oxadiazol-5(4H)-one (7.7 g, 19 mmol) in methanol (80 mL) was added sodium iodide (17.4 g, 116 mmol). After stirring for 10 minutes, a solution of chlorotrimethylsilane (14.8 mL, 116 mmol) was added dropwise over 5 minutes. The reaction continued to stir for 1 hour, at which time it was slowly added to a solution of sodium thiosulfate (23.0 g, 145 mmol) in water (800 mL) at 0° C., resulting in a precipitate. The flask was rinsed with methanol (10 mL) and the precipitate was collected through vacuum filtration. The solid was rinsed with cold water (2×25 mL) and was dried under vacuum to give the desired product (5.8 g, 60%) as the hydroiodide salt. LCMS calculated for C11H12BrN6O4 (M+H)+: m/z=370.9, 372.8. 1H NMR (400 MHz, DMSO-d6): δ 7.86 (s, 1 H), 7.36 (br s, 3 H), 6.68 (t, J=5.8 Hz, 1 H), 6.65 (s, 1 H), 5.07 (s, 2 H), 3.45 (q, J=5.8 Hz, 2 H), 2.98 (t, J=5.8 Hz, 2 H).

Provenance & Evidence