Benzeneacetonitrile, 2-fluoro- → 3-(2-fluorophenyl)[1,2,3]triazolo[1,5-a]quinazolin-5(4H)-one

Participants

Reaction Steps

Sodium (0.55 g, 24 mmol) was dissolved in dry ethanol (25 ml) at room temperature under nitrogen. 2-Fluorophenylacetonitrile (1.9 ml, 15 mmol) was added and the orange solution was stirred for 15 min, followed by dropwise addition of a solution of 2-azidobenzoic acid (1.97 g, 12.1 mmol) in diy ethanol (20 ml). The thick, white gel was stirred at room temperature for 45 min then refluxed for 18 h. Solvent was removed by evaporation and water (40 ml) was added. The yellow suspension was acidified with aqueous citric acid (1 M). The precipitate was collected, washed with water and dried in vacuo at room temperature to give 3-(2-fluorophenyl)-1,2,3-triazolo[1,5-α]quinazolin-5-one (3.38 g, 100%) as an off-white powder, m.p. 238-241° C. (DMF). Found: C, 64.33; H, 3.06; N, 20.29. C15H9FN4O requires C, 64.28; H, 3.24; N, 19.99%. δH (360 MHz; DMSO) 7.33-7.38 (2H, m), 7.46-7.55 (1H, m), 7.69-7.73 (2H, m), 8.02 (1H, ddd, J=9, 9 and 1), 8.24 (1H, dd, J=8 and 1), 8.38 (1H, d, J=8) and 12.40 (1H, br s); m/z (ES+) 821 (M+H+).

Provenance & Evidence