Aniline → HCID 791000, compound

Participants

Reaction Steps

To a mixture of (4-chloro-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine (3.97 g, 14.4 mmol), potassium carbonate (2.20 g, 15.9 mmol) and 18-crown-6 (46 mg, 0.17 mmol) in toluene (25 ml), cooled in an ice bath, was added a solution of aniline (1.4 ml, 15.4 mmol) in toluene (10 ml) over 15 minutes. After stirring at room temperature for 24 hours, the mixture was treated with ethyl acetate (35 ml) and filtered through a pad of celite under suction. The filtrate was concentrated under vacuum and the residue was recrystallized (chloroform) to give 6-Chloro-N-(4-chlorophenyl)-N′-phenyl-[1,3,5]triazine-2,4-diamine (2.20 g, 46% yield) as a white solid. 1H NMR (d6-DMSO) δ 10.1–10.4 (2H, br s), 7.5–7.8 (4H, br s), 7.3–7.5 (4H, m), 7.15–7.05 (1H, m), ESMS m/z 330 (M-H)−.

Provenance & Evidence