[CH3:1][C:2](=O)[CH2:3][CH2:4][C:5](=O)[CH3:6].I.[NH:10]([C:12]1[NH:13][CH2:14][CH2:15][N:16]=1)[NH2:11].[OH-].[K+].[C:19]([OH:26])(=[O:25])/[CH:20]=[CH:21]\[C:22]([OH:24])=[O:23]>CCOCC.C(Cl)Cl.C1C=CC=CC=1.C(O)C>[C:19]([OH:26])(=[O:25])/[CH:20]=[CH:21]\[C:22]([OH:24])=[O:23].[CH3:1][C:2]1[N:11]([NH:10][C:12]2[NH:16][CH2:15][CH2:14][N:13]=2)[C:5]([CH3:6])=[CH:4][CH:3]=1To a boiling solution of 8.63 g. (0.0756 mole) of 2,5-hexanedione in 50 ml. of absolute ethanol, a solution of 14 g. (0.0614 mole) of 2-hydrazino-4,5-dihydro-1H-imidazole hydroiodide and 3.47 g. (0.0620 mole) of potassium hydroxide in 120 ml. of absolute ethanol and 60 ml. of anhydrous benzene is quickly added. The mixture is stirred under reflux for 30 minutes and at room temperature for 12 hours. The potassium iodide which forms is cast off by filtration, then the mixture is concentrated to small volume by evaporating off the solvent. A residue is obtained which is dissolved with methylene chloride. To the obtained solution an ether solution of maleic acid is added and a precipitate readily forms, which is recrystallized two times from absolute ethanol. Yield 1.3 g. M.p. 177°-8°C. The free base melts at 192°-3°C (from methanol.
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