Phenyl Isothiocyanate → HCID 178527841, compound

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Reaction Steps

Phenyl Isothiocyanate (22 mL, 0.184 mol) is added slowly to a solution of 2-(aminomethyl)-pyridine (19 mL, 0.184 mol) in xylenes (180 mL) with cooling on ice. The resulting solution is heated at reflux for 3 h, and then allowed to cool to RT overnight. The resulting suspension is cooled to 0° C. and the solid is collected by filtration. The solid is washed with toluene and ether, and dried under vacuum to yield imidazo[1,5-a]pyridine-3-thiol as a green solid: 1H-NMR (CDCl3) δ 12.9 (br s, 1H), 8.25 (dd, J=7.5, 0.9, 1H), 7.21 (d, J=9.3, 1H), 7.06 (s, 1H), 6.75 (dd, J=9.3, 6.3, 1H), 6.59 (dt, J=7.5, 0.9); MS (M+1)+ 151.

Provenance & Evidence