Ammonia → 10-(3-Chloropropyl)-2-(trifluoromethyl)-10H-phenothiazine

Participants

Reaction Conditions

Reaction Steps

Into a 5 liter reactor fitted with stirring and cooling means and maintained at about -40° C., there were poured 1 liter of liquid ammonia, 11.5 g (0.5 mole) of metallic sodium, 0.5 g of ferric acetate and then, slowly, 133.5 g (0.5 mole) of 2-trifluoromethyl-phenothiazine. The mixture was stirred for one hour and there were added 78.8 g (0.5 mole) of 1-bromo-3-chloropropane. After stirring for some minutes, the mixture was allowed to warm slowly up to room temperature, with elimination of the liquid ammonia. There were then added 2 liters of heptane and stirring was maintained for 12 hours. The mixture was then refluxed for one hour and filtered, washed with heptane, evaporated to dryness and recrystallized from heptane to give 270 g (yield 81%) of N-(γ-chloropropyl)-2-trifluoromethyl-phenothiazine.

Provenance & Evidence