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) then nitrile (5c) (133 mg, 0.38 mmol). The mixture was stirred 10 min and was heated to reflux. After refluxing 5 h the mixture was diluted with 1N HCl, and was extracted with EtOAc. The combined organic layers were washed with water and dried (MgSO4). The solvent was removed under reduced pressure and the residue was chromatographed (silica gel, 10-20% methanol/CH2Cl2) to give the tetrazole (5d, compound XIX, R3=H, R6=H 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