[F:1][C:2]1[CH:3]=[C:4]([C:8](=O)[C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.I.[NH2:14][NH:15][C:16]([NH:19][NH:20][CH3:21])=[N:17][CH3:18].[OH-].[Na+]>C(O)C.Cl>[CH3:18][NH:17][C:16]1[N:19]([NH:20][CH3:21])[C:9](=[O:11])[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[N:14][N:15]=13.8 g (0.02 mole) of 3-fluorophenylglyoxylic acid in 10 ml of ethanol are slowly added dropwise to a solution of 5.4 g (0.022 mole) of 1-amino-2-methyl-3-methylaminoguanidine hydroiodide in 55 ml of 2N hydrochloride acid. The temperature rises from 20° to 30° C. during this addition and a pale yellow precipitate forms. This mixture is stirred for 2 hours to a temperature in the range from 60° to 70° C., whereupon a clear yellow orange solution forms. After cooling, this solution is neutralised with an aqueous solution of sodium hydroxide. The precipitate is then isolated, washed with water and dried at 70° C., affording 4.3 g (76% of theory) of 3,4-bis(methylamino)-6-(3-fluorophenyl)-4H-1,2,4-triazin-5-one with a melting point of 173°-174° C.
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