4-Chloroaniline → HCID 58065298, compound

Participants

Reaction Steps

To a solution of 262 mg (1 mmol) of (2,4-dicholoro-6-(2,6-difluorophenyl)-1,3,5-triazine (XXV) in 3 mL of dry THF was added at room temperature 129 mg (1 mmol) of iPr2NEt (Hunig's base) in 0.5 mL of dry THF. To this was added dropwise a solution of 127 mg (1 mmol) of 4-chloroaniline in 1.5 mL of dry THF. The reaction was stirred for 12 hr at room temperature and poured into a mixture of ethyl acetate and saturated aqueous sodium bicarbonate. The layers were separated. The aqueous layer was extracted twice with additional ethyl acetate and the combined organic layers were dried over magnesium sulfate. Filtration and evaporation provided a viscous film. The material was redissolved in dichloromethane and loaded onto a small plug of silica gel in a filter funnel. The silica gel was eluted with 10% ethyl acetate in hexanes and then 20% ethyl acetate in hexanes to afford 140 mg of the desired product (XXVI). ESI/MS 353.0, 354.9, 356.9 (M+H), 351.0, 353.0, 355.0 (M−H).

Provenance & Evidence