Hydrochloric Acid → HCID 89525769, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(2H-tetrazol-2-yl)aniline (2 g, 12.41 mmol) and hydrochloric acid (3.52 mL, 42.8 mmol) in acetonitrile (124 mL) and acetic acid (7 mL) stirred at −10° C., sodium nitrite (2.349 mL, 14.89 mmol) was added dropwise. The resulting mixture was stirred at 0° C. for 10 minutes, after which sulfur dioxide/acetic acid (saturated) (44 mL, 12.41 mmol) was added dropwise to the resulting mixture at a rate such that the reaction temperature is maintained below 5° C. Following the addition of SO2, a solution of copper(II) chloride dihydrate (3.61 mL, 15.51 mmol) was added dropwise. The reaction mixture was allowed to react at 0° C. for 30 minutes and then was warmed to room temperature and stirred at room temperature for 3 hours. The mixture was poured onto 400 g of ice and stirred until all the ice melted. The solid was collected by filtration and washed with water and air-dried to afford the title compound. 1H NMR (400 MHz, acetone-d6): δ 9.15 (s, 1H), 8.62 (d, 2H), 8.48 (d, 2H).

Provenance & Evidence