Water → HCID 178448417, compound

Participants

Reaction Steps

A slurry of 9-butyl-3,6-dicyanocarbazole (4 g, see Example 1C) and sodium hydride (50% in oil, 1.41 g) in 20 ml of anhydrous dimethylsulfoxide is treated dropwise with m-trifluoromethylaniline (4.72 g). The reaction mixture is stirred at room temperature for four days and then poured into 500 ml of water and stirred vigorously for two hours. The resultant precipitate is collected by filtration and purified by column chromatography using one liter of silica gel. Elution with dichloromethane and 1% ethyl acetate/dichloromethane yields 1.8 g of 9-butyl-6-cyano-N-[3-(trifluoromethyl)-phenyl]-9H-carbazole-3-carboximidamide. Elution with 20% ethyl acetate/dichloromethane and ethyl acetate/dichloromethane/methanol (2:7:1) yields 1.6 g of the desired diamidine, which is recrystallized from two liters of water containing 15 ml of 10% hydrochloric acid to yield 1.5 g of the title compound, melting point 205°-210° C.

Provenance & Evidence