[CH3:1][C:2]1[N:3]=[N:4][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][N+:7]=1[O-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[NH3:26]>C(Cl)(Cl)Cl.O1CCOCC1>[NH2:26][C:6]1[N:7]=[C:2]([CH3:1])[N:3]=[N:4][C:5]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1To 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).
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