Cl.[NH:2]([C:6]1[S:7][CH:8]=[C:9]([CH2:11][S:12][CH2:13][CH2:14][NH2:15])[N:10]=1)[C:3]([NH2:5])=[NH:4].C(N(CC)CC)C.[CH3:23][N:24]=[C:25]=[S:26].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31]>CO.CC(C)=O>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31].[NH:2]([C:6]1[S:7][CH:8]=[C:9]([CH2:11][S:12][CH2:13][CH2:14][NH:15][C:25]([NH:24][CH3:23])=[S:26])[N:10]=1)[C:3]([NH2:5])=[NH:4]A suspension of 2-guanidino-4-[(2-aminoethyl)thiomethyl]thiazole hydrochloride (1.52 g.) in methanol (30 ml.) was treated with triethylamine (1.01 g.) to give a pale yellow solution. Methyl isothiocyanate (0.365 g.) was added and the solution stirred for 16 hours at room temperature. Evaporation of the solvent gave a gum which was dissolved in acetone (20 ml.) and treated with maleic acid (1 g.) in acetone (20 ml.). The precipitate was filtered off and recrystallized from ethanol to give 2-guanidino-4-[2-(3-methylthioureido)ethylthiomethyl]thiazole hydrogen maleate as a pale brown solid (0.420 g.). Found: C, 37.4; H, 4.7; N, 19.8; S, 22.7. C13H20N6S3O4 requires C, 37.14; H, 4.76; N, 20.00; S, 22.85%.
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