Dimethylformamide → HCID 20041224, compound

Participants

Reaction Steps

A solution of 34.2 g (0.2 mol) of p-toluenesulfonamide in 100 ml of dry N,N-dimethylformamide was added dropwise to a suspension of 18.9 g (0.42 mol) of sodium hydride (50% oil dispersion) in 60 ml of N,N-dimethylformamide. The reaction was stirred at room temperature for one hour, followed by one hour at 60° C. A solution of 52.8 g (0.2 mol) of α,α'-dibromo-0-xylene in 300 ml of N,N-dimethylformamide was added at such a rate that the temperature of the reaction mixture remained between 60°-70° C. After further stirring for 48 hours at room temperature under nitrogen ice water was added to the reaction mixture. The precipitated solid was filtered and recrystallized from hot ethanol. Yield 33.58 g, m.p. 175°-177° C. NMR (CDCl3) δ 2.32 (3H, s), 4.5 (4H,s), 7.25 (8H, m).

Provenance & Evidence