N-Methylaniline → N-Methylaniline

Participants

Reaction Steps

Freshly distilled N-methylaniline (b.p. 196° C.) is prepared. To 1.07 g (0.01 mole) of the N-methylaniline is added 2.56 g (0.01 mole) of 2-bromobenzenesulfonyl chloride (98 w/w %). The mixture is stirred until hot. Ten percent sodium hydroxide is then added dropwise with stirring until the solution is slightly alkaline, and 2-bromo-N-methylbenzenesulfonanilide is formed as a viscous red-brown liquid. It is washed with water several times until the wash water is neutral to litmus paper. A viscous red-brown liquid is extracted with ether, and the ether layer is dried over magnesium sulfate, filtered and the solvent removed by evaporation. The yield of red-brown oil is 2.30 g (70% yield). 1H NMR (deuterioacetone): δ 7.1-8 (m, 9 ArH), 3.3 (s, 3H, N—CH3).

Provenance & Evidence