Ammonia → 3-Methyl-6-phenyl-1,2,4-triazin-5-amine

Participants

Reaction Steps

To a solution of 3-methyl-6-phenyl-[1,2,4]triazine-4-oxide (3 g, 16 mmol) in chloroform (80 ml) was added p-toluenesulfonyl chloride (3.05 g, 16 mmol) and the mixture stirred under nitrogen at room temperature for 30 min. To this mixture was added aqueous ammonia (48 ml of 12%) and ammonia in dioxane (160 ml of a 0.5 M solution) and stirred at room temperature for 72 h. The organic layer was separated from the aqueous which was extracted with dichloromethane (2×20 ml), the combined organic layers dried over MgSO4 and evaporated in vacuo. The residue was purified by flash chromatography (SiO2; 20% EtOAc in hexanes) to afford the title compound (1.7 g). δH (400 MHz; d6-DMSO) 2.42 (3H, s), 6.50-7.40 (2H, vbs), 7.49-7.63 (5H, m). m/z (ES+) 187 (M+1).

Provenance & Evidence