Ammonium Chloride → HCID 178510078, compound

Participants

Reaction Conditions

Reaction Steps

Ammonium chloride (0.46 g, 8.5 mmol) and sodium azide (0.55 g, 8.5 mmol) were added to a solution of 4-(2-aminophenoxy)phthalonitrile (0.5 g, 2.1 mmol) in DMF (20 ml). The reaction mixture was heated at 80° C. for 48 hours, cooled to room temperature and evaporated to dryness in vacuo. The crude compound was purified on silica gel (eluent: methylene chloride:methanol (4:1)) to give 2-[3-cyano-4-(1H-tetrazol-5yl)phenoxy]aniline or 2-[4-cyano-3-(1H-tetrazol-5-yl)phenoxy]aniline as yellow crystals (yield: 0.64 g (95%)). 1H—NMR (CD3OD) in ppm: δ 5.2 (2H,s), 6.6 (1H, d,d), 6.85 (1H,d,d), 6.95 (1H,d,d.), 7.0 (1H,d,d.), 7.45 (1H,d), 7.65 (1H,d). 13C—NMR (CD3OD) in ppm: δ 105.3; 118.7; 119.4; 119.7; 120.7; 123.0; 128.3; 133.3; 138.3; 138.3; 140.7; 142.8; 158.9; 163.4.

Provenance & Evidence