Acetic Acid → 1-(3-bromophenyl)-2-methylpropan-2-amine

Participants

Reaction Steps

A solution of N-[2-(3-bromophenyl)-1,1-dimethylethyl]-2-chloroacetamide (Preparation 30) (32.0 g, 105 mmol), thiourea (9.60 g, 126 mmol) and acetic acid (50 ml) in ethanol (250 ml) was heated to reflux overnight. The reaction mixture was cooled to room temperature and filtered, the filtrate was concentrated in vacuo and basified using aqueous sodium hydroxide solution (1M, 450 ml). The product was extracted with dichloromethane (2×500 ml) and the combined organics washed with brine (50 ml), dried (sodium sulfate) and the solvent removed in vacuo to afford the title compound as a black oil (23 g). 1H NMR (400 MHz, CDCl3) δ=7.36-7.32 (2H, m), 7.16-7.08 (2H, m), 2.62 (2H, s), 1.84 (2H, bs), 1.12 (6H, s). LRMS (electrospray) m/z 228 [M+H]+

Provenance & Evidence