Potassium Carbonate → O-2-naphthyl N-methyl-N-(6-methyl-2-pyridyl)thiocarbamate

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Reaction Steps

To a mixture of 1.22 g of 6-methyl-2-methylaminopyridine and 1.38 g of anhydrous potassium carbonate in 20 ml of acetone was added dropwise 2.23 g of 2-naphthylchlorothioformate in 20 ml of acetone under agitation at room temperature. The reaction mixture was stirred overnight at room temperature and inorganic salts were removed by filtration. After acetone was removed by distillation under a reduced pressure, the residue was purified by the column chromatography (silica gel, developed with ethyl acetate/benzene=1/9 (V/V), to obtain 2.62 g of O-2-naphthyl N-methyl-N-(6-methyl-2-pyridyl)thiocarbamate as a solid in a yield of 85%. A portion of the product was recrystallized from ethanol to give colorless crystals having a melting point of 149.5° C.-150.5° C. Elemental analysis of the crystals is given below.

Provenance & Evidence