Dimethylformamide → 4-Chloro-2-chloromethyl-3-methoxypyridinium chloride

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The resulting solution of 4-chloro-2-hydroxymethyl-3-methoxypyridine (−30% strength) was diluted with CH2Cl2 (48 L). DMF (65.5 g, 0.896 mol) was added in one portion and, then, thionyl chloride (11.1 kg, 93.2 mol) over 3-5 h at 15-30° C. After stirring for additional 1.5 h, about 45 L of solvents were distilled off. Toluene (20 L) was added and 20 L of solvents were again removed by distillation. Then, ethanol (1.5 L) was added to the resulting thick slurry. The solids were filtered off at 10-15° C., washed with toluene (17 L) and dried in vacuo at 30° C. to give 4-chloro-2-chloromethyl-3-methoxypyridinium chloride as an off-white solid (m. p. 132° C.); yield 15.0 kg (59%).

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