Dimethylformamide → N,N-Dimethyl-N′-octylmethanimidamide

Participants

Reaction Steps

Dimethylformamide (8.8 g, 0.12 mole), dimethyl sulfate (19.3 g, 0.15 mole) and toluene (20 ml) were placed in a 100 ml round bottom flask and heated at reflux for 30 minutes. During this time a light brown oil separated. The reaction was cooled to room temperature and the toluene was decanted. The dimethylformamide/dimethyl sulfate complex was washed with dry toluene (2×20 ml) and the toluene was decanted. n-Octylamine (15.5 g, 0.12 mole) in toluene (20 ml) was added rapidly with stirring. The reaction temperature rose briefly to 60° C. The reaction was stirred for 90 minutes, then extracted with a solution of sodium hydroxide (7.2 g, 0.18 mole) in water (40 ml). The organic phase was washed with brine (40 ml), dried over anhydrous Na2SO4, and filtered. GLC showed the product to be about 72% pure after concentration.

Provenance & Evidence