反应详情

温度

75 °C

Triethyl orthoformate (28.79 ml, 25.65 g, 173 mmol) was added to a stirred, heated (80° C.) solution of 1-(5-amino-2-methoxyphenyl)ethanone (8.16 g, 49 mmol) in acetic acid (80 ml) and the mixture was stirred at 75° C. for 1 hour. Sodium azide (9.64 g, 148 mmol) was added in portions over 90 minutes, then the mixture was stirred at 75° C. for 4 hours. The mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. Hydrochloric acid (1M, 100 ml) was added and the mixture was stirred at room temperature 1 hour. The solid was collected, flushed with toluene (100 ml) and dried in vacuo at room temperature. The residue was recrystallized from ethanol (700 ml) to give 1-[2-methoxy-5-(1H-tetrazol-1-y1)phenyl]ethanone as tan coloured needles (7.88 g, 73%), 1H NMR (d6 -DMSO) δ 10.06 (1H, s), 8.06 (2H, m), 7.46 (1H, d, J=7.8 Hz), 3.99 (3H, s), and 2.60 (3H, s). m/e (CI+) 219 (MH+)

1. stirringthe mixture was stirred at 75° C. for 4 hours
2. temperatureThe mixture was cooled to room temperature
3. customthe solvent was evaporated under reduced pressure
4. additionHydrochloric acid (1M, 100 ml) was added
5. stirringthe mixture was stirred at room temperature 1 hour
6. customThe solid was collected
7. customflushed with toluene (100 ml)
8. customdried in vacuo at room temperature
9. customThe residue was recrystallized from ethanol (700 ml)