C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]([CH2:10][C:11]1[O:15][C:14]([CH2:16][S:17][CH2:18][CH2:19][NH2:20])=[CH:13][CH:12]=1)[CH3:9].CS[C:23](=[N:27][CH3:28])[NH:24][C:25]#[N:26]>C(#N)C.[N+]([O-])([O-])=O.[Ag+]>[C:25]([N:24]=[C:23]([NH:27][CH3:28])[NH:20][CH2:19][CH2:18][S:17][CH2:16][C:14]1[O:15][C:11]([CH2:10][N:8]([CH3:7])[CH3:9])=[CH:12][CH:13]=1)#[N:26]To a stirred suspension of potassium carbonate (20.7 g) in a solution of 2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethanamine (10.7 g) and N-cyano-N'-methylcarbamimidothioic acid methyl ester (7.1 g) in acetonitrile (107 ml) at 70° was added a solution of silver nitrate (9.35 g) in acetonitrile (20 ml) during 1 hr. The mixture was stirred for 16 hr, the solid filtered and the filtrate evaporated to dryness. The residue was dissolved in ethyl acetate (250 ml). A portion of this (10.5 ml) was washed with water (6 ml), the ethyl acetate layer evaporated to give a solid which was crystallised from isopropylacetate (1.75 ml) giving N"-cyano-N-[2-[[[5-(dimethylaminomethyl)-2-furanyl]methyl]thio]ethyl]-N'-methylguanidine (0.35 g) m.p. 79°-81.5°.
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