Cl.Cl.[NH2:3][CH:4]1[CH2:12][CH2:11][C:7]2[NH:8][CH:9]=[N:10][C:6]=2[CH2:5]1.C(N(CC)CC)C.[C:20]1([N:26]=[C:27]=[S:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>O.C(Cl)Cl.C(O)C>[C:20]1([NH:26][C:27]([NH:3][CH:4]2[CH2:12][CH2:11][C:7]3[NH:8][CH:9]=[N:10][C:6]=3[CH2:5]2)=[S:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1A mixture of 5-amino-4,5,6,7-tetrahydro-1H-benzimidazole, dihydrochloride (210 mg, 1.0 mmol), ethanol (1 ml), triethylamine (0.276 ml, 2.0 mmol) and phenylisothiocyanate (270 mg, 2.0 mmol) was stirred for 3 hours at ambient temperature. 1 N hydrochloric acid (20 ml), DCM (50 ml) and H2O (20 ml) were added. The phases were separated and the aqueous phase was washed with DCM (3×25 ml) and then made alkaline with 4 N sodium hydroxide. The alkaline mixture was extracted with DCM (2×20 ml) and the combined organic extracts were dried (magnesium sulphate). The solvent was evaporated in vacuo to give 140 mg (52%) of the title compound.
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