4-Chloroaniline → 4,6-dichloro-N-(4-chlorophenyl)-1,3,5-triazin-2-amine

Participants

Reaction Steps

To a mixture of cyanuric chloride (5.15 g, 27.9 mmol), potassium carbonate (3.98 g, 28.8 mmol) and 18-crown-6 (158 mg, 0.60 mmol) in toluene (40 ml), cooled in an ice bath, was added a solution of 4-chloroaniline (3.61 g, 28.3 mmol) in toluene (20 ml) over 15 minutes. After stirring at room temperature for 20 hours, the mixture was treated with ethyl acetate (60 ml) and filtered through a pad of celite under suction. The filtrate was concentrated under vacuum and recrystallized (chloroform) to give (4-chloro-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine (4.06 g, 53% yield) as a white solid. 1H NMR (d6-DMSO) δ 11.23 (1H, s), 7.62 (2H, d, J=9 Hz), 7.47(2H, d, J=9 Hz). 13C NMR (d6-DMSO) δ 169.5, 168.5, 163.6, 135.7, 128.6, 122.5, ESMS m/z 273 (M−H)−.

Provenance & Evidence