Sodium Azide → HCID 59414873, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 11 (2.3 g, 10.5 mmol) in dry DMSO (15 mL) was added NaN3 (1.0 g, 15.7 mmol). The reaction solution was allowed to stir at 65° C. for 4 h then cooled to room temperature. The reaction mixture was partitioned between EtOAc (300 mL) and H2O (200 mL). The organic layer was washed with H2O (200 mL), brine (200 mL), and dried over Na2SO4. The solvents were removed by rotary evaporation and the crude product was purified by flash column chromatography (EtOAc/hexanes, 1:18-1:9) to yield 12 (1.6 g, 85%) as a yellow oil: 1H NMR (500 MHz, CDCl3) δ 3.40-3.50 (dd, J=3.0, 13.5, 0.5H), 3.50-3.60 (dd, J=3.0, 13.5 Hz, 0.5H), 3.60-3.75 (m, 1H), 5.50-5.60 (dd, J=3.0, 8.0 Hz, 0.5H), 5.65-5.80 (dd, J=3.0, 8.0 Hz, 0.5H), 7.00-7.20 (m, 3H), 7.30-7.50 (m, 1H); 13C NMR (125 MHz, CDCl3) δ 55.9, 56.1, 91.82, 91.84, 93.2, 93.3, 112.78, 112.84, 112.96, 113.03, 116.19, 116.20, 116.36, 116.38, 121.24, 121.27, 121.30, 121.33, 130.7, 130.8, 139.09, 139.15, 139.25, 139.31, 162.1, 164.1; GC-MS calcd for C8H7F2N3 183. found 183.

Provenance & Evidence