Hydrochloric Acid → 1-(2-Fluoro-4-biphenylyl)ethyl-2-dimethylaminothiazole

Participants

Reaction Steps

To 4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-methylaminothiazole (415 mg, 1.33 mmol) in benzene (6 ml) was added methyl iodide (370 mg, 2.61 mmol), tetra-n-butyl ammonium hydrogene sulfate (435 mg, 1.33 mmol) and 50% NaOH aq. (3 ml), then the mixture was stirred at room temperature overnight. The reaction mixture was diluted with water, then acidified with 2N-HCl to pH 6 and the aqueous solution was extracted with benzene. The extracts were washed with water, dried and then evaporated under reduced pressure to a residue, which chromatographed to afford 4-(1-(2-fluoro-4-biphenylyl)ethyl-2-dimethylaminothiazole (369 mg, 85% yield): NMR(CDCl3)δ 1.62(d, 3H), 3.06(s, 6H), 4.09(q, 1H), 6.06(s, 1H), 7.02-7.63(m, 8H) ppm; IR(neat) 2950, 1620, 1550, 1420, 1340 cm-1.

Provenance & Evidence