Hydrochloric Acid → 3-(4-Fluorophenyl)-1,2-oxazol-5-amine

Participants

Reaction Steps

(4-Fluorobenzoyl)acetonitrile (10 g., 0.063 mol) and 200 ml. of ethyl alcohol were placed in a 500 ml. 1-neck flask. To the reaction mixture was added in portionwise fashion a solution comprised of 24 g. of sodium acetate and 18.3 g. of hydroxylamine.HCl in 200 ml. of H2O. After refluxing for three days, the reaction mixture was cooled to room temperature. About half the solvent was removed and then an oily layer formed. The residue was extracted thoroughly in ether and then the combined ether extracts were washed in water, brine, and then dried over MgSO4. When the ether was removed orange crystals formed which were recrystallized from diethyl ether/hexane, m.p., 98°-99° C.

Provenance & Evidence