Water → N-[2,4-bis(methylthio)-6-methyl-pyridin-3-yl]-2-chloroacetamide

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Reaction Steps

Part A. A solution of 3-amino-2,4-bis(methylthio)-6-methylpyridine (0.38 g,1.88 mmol) and triethylamine (0.30 mL, 2.07 mmol) in tetrahydrofuran (8 mL)was cooled to 0° C., and treated with a solution of chloroacetyl chloride (0.18 mL, 2.26 mmol) in tetrahydrofuran (4 mL). After being stirred for 10 hours, the mixture was poured into water (100 mL), and thiswas extracted with ethyl acetate (2×100 mL). The extracts were combined, dried over anhydrous sodium sulfate, filtered and evaporated. The resulting solid was recrystallized to purity from ether, mp 190°-192° C., to afford N-[2,4-bis(methylthio)-6-methyl-pyridin-3-yl]-2-chloroacetamide (0.39 g, 1.41 mmol, 75%). 1H NMR (CDCl3): δ 7.69 (1H, br s); 6.68 (1H, s); 4.26 (2H, s); 2.53 (3H, s); 2.51 (3H, s); 2.43 (3H, s). Mass spectrum (NH3 -CI/DDIP): m/z 279 (42%); 278 (17%); 277 (100%); 227 (4%).

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