Sodium Azide → HCID 178438077, compound

Participants

Reaction Steps

To a solution of aluminum chloride (175 mg, 1.31 mmol) in THF (4 mL) at 0° C. was added sodium azide (170 mg, 2.61 mmol) and then nitrile (5c) (133 mg, 0.38 mmol). The mixture was stirred 10 min and heated to reflux. After refluxing 5 h, the mixture was diluted with 1N HCl and extracted with EtOAc. The combined organic layers were washed with water and dried (MgSO4). The solvent was removed under reduced pressure and the residue chromatographed (silica gel, 10–20% methanol/CH2Cl2) to give tetrazole (5d) as a white solid (84 mg, 56%): 1H NMR (CDCl3) δ 7.49 (d, J=16.8 Hz, 1H), 7.34–7.06 (m, 12H), 6.91 (d, J=8.0 Hz, 2H), 6.79 (dd, J=7.3, 1.5 Hz, 1H), 2.84 (t, J=7.0 Hz, 2H), 2.38 (t, J=7.0 Hz, 2H), 2.16 (m, 2H); ESI m/z: 389 (M−H−, 100%).

Provenance & Evidence