Methyl iodide → 2-[1-(Dimethylcarbamoyl)ethylthio]-3-phenylquinoline

Participants

Reaction Steps

To a solution of lithium di-isopropylamide [prepared from di-isopropylamine (6.2 ml.) and n-butyllithium (24.7 ml. of a 1.7 M solution in hexane) in dry tetrahydrofuran (100 ml.) at -78°. under argon] was added a solution of 2-(dimethylcarbamoylmethylthio)-3-phenylquinoline (6.6 g.) in dry tetrahydrofuran (50 ml.) at -60°. The mixture was then stirred for 15 min. at -60°. Iodomethane (2.7 ml.) was added and the mixture was allowed to warm up to ambient temperature. Glacial acetic acid (2.6 ml.) was then added, followed by water (200 ml.). The tetrahydrofuran phase was separated and retained, and the aqueous layer was extracted with ethyl acetate (2×30 ml.). The ethyl acetate and tetrahydrofuran phases were combined and dried (MgSO4). The solvent was evaporated and the residual oil was chromatographed on basic alumina (100 g. of Brockmann grade III) eluted with increasing concentrations of chloroform in petroleum ether. The eluate obtained with 20% v/v chloroform in petroleum ether on evaporation gave 2-[1-(dimethylcarbamoyl)ethylthio]-3-phenylquinoline as a viscous oil, which was used without further purification.

Provenance & Evidence