Cyanamide → HCID 15888355, compound

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Reaction Steps

To a cooled solution of 2-butyl-1,2,4-thiadiazolo[4,5-a]benzimidazole-3(2H)-one (2.00 g, 8.08 mmole) in 25 mL dichloromethane, cyanamide (0.728 g, 16.2 mmole) was added in one portion and the mixture was stirred for 48 h at room temperature. The resulting precipitate was filtered, slurried in methanol and subsequently washed with dichloromethane to give 1.01 g (66%) of 3-amino-1,2,4-thiadiazolo[4,5-a]benzimidazole as colourless crystals: mp 255-256 ° C.; 1H NMR (DMSO-d6) δ 8.23 (d, 1H), 7.71 (d, 1H), 7.43 (t, 1H), 7.54 (s, 2H), 7.32 (t, 1H) ppm; IR (KBr) ν 3302, 3151, 1661, 1577, 1487, 1473, 1251, 1207, 810 cm-1 ; HRMS calcd for C8H6N4S 190.0313, found 190.0293. Anal. Calcd for C8H6N4S: C, 50.51; H, 3.18; N, 29.45. Found: C, 50.26; H, 3.26; N, 29.38.

Provenance & Evidence