Water → S-2-Pyridyl isonicotinothioate

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Following a general procedure (Rao et al., J. Org. Chem. 2000, 65: 1084), to a suspension of isonicotinoyl chloride hydrochloride (4.45 g, 25.0 mmol) in CH2Cl2 (50 mL) was added triethylamine (7 mL, 50 mmol). The mixture was stirred for 5 min under argon. To the resulting solution was added 2-mercaptopyridine (2.77 g, 25.0 mmol) in portions over 5 min with stirring. After 1 h, water was added and the layers were separated. The organic layer was washed (2 N NaOH, then water), dried (Na2SO4) and concentrated to dryness. The solid residue was recrystallized from ethyl acetate/hexanes to afford brown crystals (4.21 g, 77%): mp 115° C.; 1H NMR δ 7.34-7.38 (m, 1H), 7.69-7.38 (m, 4H), 8.69 (m, 1H), 8.83 (m, 2H); 13C NMR δ 120.5, 124.2, 130.8, 137.5, 142.8, 150.1, 150.8, 151.1; HRMS (FAB) obsd 217.0426, calcd 217.0436 (M++H, C11H9N2OS). Anal. Calcd for C11H8N2OS: C, 61.09; H, 3.73; N, 12.95. Found: C, 60.97; H, 3.72; N, 12.95.

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