Acetic Acid → HCID 178505613, compound

Participants

Reaction Steps

The 5-(2-fluorophenyl)-1H-tetrazole starting material was prepared as follows. A 3-necked 500 ml round-bottom flask was charged with 2-fluorobenzonitrile (48.4 g, 0.4 mol), n-butanol (160 ml), NaN3 (34.3 g, 0.528 mol) and glacial acetic acid (31.7 g, 0.528 mol). The mixture was warmed to a mild reflux for 24 h under nitrogen behind a safety shield. After the mixture had cooled to room temperature, it was again charged with NaN3 (34.3 g, 0.528 mol) and glacial acetic acid (31.7 g, 0.528 mol). The mixture was warmed to a mild reflux for an additional 24 h under nitrogen, cooled and then diluted with diethyl ether (320 ml). This organic mixture was extracted with 2N NaOH (4×100 ml) and the combined ice-cold basic extracts were carefully acidified to pH 1 with concentrated hydrochloric acid. The product was isolated as a light gray solid (45.2 g, 68.9%) after drying under vacuum at 60° C., mp 160.5°-162° C. [lit. mp 160°-162° C.; George, E. F. and Riddell, W. D., U.S. Pat. No. 3,865,570 (Feb. 13, 1973)]. There was obtained a second crop of product (1.0 g, 1.5%). A 1.0 g sample of this material was crystallized from water to produce a white solid, mp 162.5°-163.5° C.

Provenance & Evidence