Sodium Azide → HCID 16107468, compound

Participants

Reaction Conditions

Reaction Steps

Sodium azide (4.4 g, 66.9 mmol) was added to a stirred solution of compound 10 (21.2 g, 33.4 mmol) in dimethylformaldehyde (120 mL). The reaction mixture was stirred at 60° C. for 4 hours. The solvent was removed under vacuo and the residue was dissolved in tetrahydrofuran (120 mL). Sulfuric acid (0.87 mL) and water (0.32 mL) were added to the stirred tetrahydrofuran solution and the resulting mixture was stirred at room temperature for an additional hour. After removal the solvent, the residue was redissolved in dichloromethane (200 mL) and extracted with perfluorohexane (100 mL 4 times). The combined extraction was washed with dichloromethane (10 mL) and concentrated under vacuo to give the pure azide 11 as a clear oil (19.3 g, 97%). 1H NMR (400 MHz, CDCl3) δ 3.47 (s, 2H), 3.63 (s, 2H), 4.02 (s, 4H); 19F NMR (376 MHz, CDCl3) δ −73.21 (s); 13C NMR (100.7 MHz, CDCl3) δ 45.8, 49.8, 60.2, 66.8, 79.6 (m), 120.2 (q, J=293.3 Hz); MS (CI) m/z 598 (M++1, 72), 570 (100); HRMS (CI) Calcd for C13H10F18N3O3: 598.0435, Found: 598.0418.

Provenance & Evidence