Triethylamine → N,N-diethyl-3-(N',N'-diethylthiocarbamoyloxy)picolinamide

Participants

Reaction Conditions

Reaction Steps

258.3 g (1.33 mol) of 3-hydroxy-N,N-diethylpicolinamide are introduced into 1 l of dimethylpropyleneurea and 213.2 ml (1.53 mol) of triethylamine at 0° C., and 222 g (1.464 mol) of diethylthiocarbamoyl chloride are introduced in the form of a solid. After the reaction mixture has been stirred for 2 hours at 0° C., it is poured into 2 l of water and extracted three times using ethyl acetate, the ethyl acetate phases are washed five times using 500 ml of water in each case, and the combined organic phases are dried over Na2SO4 and concentrated in vacuo at 60° C. Recrystallization from Et2O/hexane gives 341 g (83%) of brown crystals, m.p. 70°-72° C.

Provenance & Evidence