Dibutyltin oxide → HCID 178507487, compound

Participants

Reaction Steps

To 2-cyanoaniline (5.00 g, 42.3 mmol) and dibutyltin oxide (520 mg, 2.1 mmol) dissolved in toluene (40 mL) was added trimethylsilyl azide (6.40 mL, 47 mmol). The reaction mixture was heated at ~95° C. for 70 hours, cooled to ambient temperature, concentrated under reduced pressure and partitioned between water (50 mL) and saturated sodium carbonate solution (50 mL). The organic phase was extracted with another aliquot (25 mL) of saturated sodium carbonate solution. The combined aqueous extracts were washed with ether (2×25 mL), acidified with solid citric acid to pH 4-5, and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine, dried over magnesium sulfate, decolorized with Norite, filtered and concentrated under reduced pressure to give the title compound as a solid (1.20 g). 1H NMR (DMSO-d6, 300 MHz) δ3.4 (br s, 1H), 6.68 (dt, J=1 Hz, 8 Hz, 1H), 6.90 (d, J=8 Hz, 1H), 7.25 (d,t J=1 Hz, 8 Hz, 1H), 7.73 (d, J=8 Hz, 1H), 9.0-11.0 (br, 2H). MS (DCl/NH3) m/e 162 (M+H)+, 179 (M+H+NH3)+.

Provenance & Evidence