Benzoyl isothiocyanate → 4-{[(benzoylamino)carbonothioyl][(2-butyl-4-chloro-1H-imidazol-5-yl)methlyl]amino}-1H-imidazole-5-carboxamide

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Reaction Steps

4-{[(2-Butyl-4-chloro-1H-imidazol-5-yl)methyl]amino}-1H-imidazole-5-carboxamide (0.30 g, 1.01 mmol, obtained from Example 7(a)) was dissolved in CH2Cl2 (5 mL) and methanol (2 mL). Benzoylisothiocyanate (0.18 g, 1.11 mmol) was added and the mixture was stirred at r.t. for 4 h. The mixture was then concentrated in vacuo and dissolved in ethyl acetate and washed with water. The aqueous phase was extracted twice with ethyl acetate and the combined organic layers were dried (MgSO4) and concentrated. The crude product was purified by flash column chromatography (CH2Cl2/methanol gradient; 0 to 20% methanol), obtaining 0.175 g (38%) of the title compound. MS (ESI) m/z 460 (M+1).

Provenance & Evidence