Triethylamine → Phenyl (2-chloropyridin-4-yl)carbamate

Under a dry nitrogen atmosphere a solution of 12.0 ml (0.096 mole) of phenyl chloroformate in 300 ml of methylene chloride was added dropwise to a cold (0° C.) stirred solution of 10.2 g (0.079 mole) of 4-amino-2-chloropyridine and 16.5 ml (0.12 mole) of triethylamine in 300 ml of methylene chloride. After complete addition the reaction mixture was allowed to come to room temperature and stirred at room temperature for approximately 18 hours. The mixture was washed with three 100 ml portions of water followed by 100 ml of an aqueous saturated sodium chloride solution. The washed mixture was dried over anhydrous magnesium sulfate and filtered. The filtrate was subjected to column chromatography on silica gel, eluted with acetone:methylene chloride (4:96), to yield 7.4 g of phenyl N-(2-chloro-4-pyridinyl)carbamate as a solid.