Trifluoroacetic acid → N-[1-[1-(6-Chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoroacetamide

Participants

Reaction Conditions

Reaction Steps

In 100 ml of toluene, 10.0 g (0.106 mol) of 2-aminopyridine was dissolved. After the solution was cooled to 5° C., 11.8 ml (0.159 mol) of trifluoroacetic acid and subsequently 7.76 ml (0.106 mol) of thionyl chloride were added thereto portionwise, followed by stirring at room temperature overnight. Then, 50 ml of toluene was distilled off under reduced pressure. To the reaction liquid, 50 ml of toluene was added. Then, 50 ml of dimethylformamide, 22.03 g (0.16 mol) of potassium carbonate powder, and 17.56 g (0.108 mol) of 2-chloro-5-chloromethylpyridine were added thereto under ice-cooling. Then, distillation was conducted under reduced pressure (90 to 36 hPa) at 60° C. for 1.5 hours. To the reaction liquid, 30 ml of methanol and 20 ml of water were added. The reaction liquid was added to 300 ml of water of 50° C., while the vessel was also washed. The mixture was stirred at room temperature for 30 minutes, and then the crystals were filtered, and washed with 50 ml of water and 30 ml of toluene. The obtained crystals were dried under reduced pressure at 60° C. Thus, 21.45 g of the target compound was obtained (64.1%).

Provenance & Evidence