Toluene → tert-Butyl (6-(chloromethyl)pyridin-2-yl)carbamate

Participants

Reaction Steps

2.43 g (10 millimoles) of 2-amino-6-chloromethylpyridine, toluene (30 mL), 10 mL of t-butyl alcohol and 1.48 g (5 millimoles) of triphosgene were added to a reaction system followed by refluxing for 1 hour. Water and 28% sodium hydroxide were sequentially added while holding the internal temperature at 0° C. or lower. After separating the liquid, the aqueous phase was extracted with ethyl acetate. The organic phases were combined and mixed. A portion of the organic phase was sampled and subjected to quantitative analysis by HPLC. The target (6-chloromethyl-pyridin-2-yl)-carbamic acid tert-butyl ester was not formed at all. 1,3-bis-(6-chloromethyl-pyridin-2-yl)-urea (urea compound) constituted the main product.

Provenance & Evidence