[C:1]([NH:3][C:4]([NH:6][CH3:7])=S)#[N:2].[CH3:8][C:9]1[NH:13][CH:12]=[N:11][C:10]=1[CH2:14][S:15][CH2:16][CH2:17][NH2:18].S([O-])([O-])(=O)=O.[Na+].[Na+]>CC#N>[C:1]([N:3]=[C:4]([NH:18][CH2:17][CH2:16][S:15][CH2:14][C:10]1[N:11]=[CH:12][NH:13][C:9]=1[CH3:8])[NH:6][CH3:7])#[N:2]A suspension of N-cyano-N'-methylthiourea (DBU salt) (0.534 g), 2-(5-methylimidazol-4-ylmethylthio)ethylamine (1.03 g), HgO (0.868 g) and anhydrous sodium sulfate (2 g) in CH3CN (20 ml) was heated under reflux for 20 hrs. with vigorous stirring. The hot reaction mixture was filtered and the filtrate was dried up and subjected to chromatography on SiO2 [eluant: CH3CN-CH3OH (4:1)]. The resulting crude product was purified by preparative thin layer chromatography [SiO2, AcOEt--MeOH--28% aq. NH3 (10:1:1)] and recrystallized from CH3CN to give N"-cyano-N-methyl-N'-[2-(5-methylimidazol-4-ylmethylthio)ethyl]-guanidine (38.4 mg). Yield 7.6%, m.p. 136°-138° C.
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