Dimethylformamide → HCID 67104421, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-methyl-3-nitrobenzoic acid (36.23 g, 0.2 mmol), N,N-dimethylformamide (5 mL), and toluene (85 mL) was added with stirring thionyl chloride (30 mL, 48.8 g, 0.41 mole). The mixture was stirred at gentle reflux for four hours, then distilled to approximately half the volume (67.77 g residual net weight) to remove excess thionyl chloride. This solution was cooled to 20° C., and 22.6 grams of it (nominally 6.67 mmol) was added to a solution of N,N-di-n-propylamine (22.0 g, 0.22 mole) in ethyl acetate (100 mL) resulting in immediate formation of a slurry that was stirred at ambient temperature overnight. This was then quenched into water (150 mL). The organic layer was washed with cold 0.5 N hydrochloric acid (100 mL), then with 5% aqueous sodium bicarbonate, dried (MgSO4) and evaporated to give a colorless oil weighing 16.55 g (94.0%). This was characterized by proton and carbon nmr, as well as electrospray mass spectrum (M+1 at m/e 265.1).

Provenance & Evidence