Water → N-(pyridin-2-yl)-5-thiocyanatothiazol-2-amine

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To a suspension of N-(pyridin-2-yl)thiazol-2-amine (4.26 g, 24 mmol) and sodium thiocyanate (3.9 g, 48 mmol, 2 eq) in methanol (100 mL) at 0° C., was slowly added bromine (1.23 mL, 24 mmol, 1 eq) over 2 min, then the temperature was raised to 23° C. and the mixture was stirred for 3 h. The resulting suspension was added to stirring cold water (400 mL) and the resulting precipitate was collected by filtration and vacuum dried (4.5 g, 80%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.00-7.08 (1 H, m), 7.11 (1 H, d, J=8.34 Hz), 7.74-7.84 (1 H, m), 7.89 (1 H, s), 8.39 (1 H, d, J=5.05 Hz), 11.93 (1 H, s). LC/MS (M+H)+: 235.

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