Triethylamine → HCID 19890950, compound

Participants

Reaction Steps

To a solution of 5.84 g (0.02 mol) 2-(2-picolylseleno)benzoic acid (from Example 1) in 40 ml dichloromethane that has been cooled to 0° C. are added in one portion 5 g (0.02 mol) bis[2-oxo-3-oxazolidinyl]phosphoryl chloride. After stirring for 2 hours at room temperature 1.88 g (0.02 mol) 2-aminopyridine, 50 ml dichloromethane and 6.4 ml triethylamine are added dropwise in succession at 10° C. and stirring is continued at room temperature for 20 h. The reaction mixture is extracted twice with 100 ml portions of water, dried over sodium sulfate and the solvent removed. The brown oil (7 g) is taken up in 100 ml 1 N HCl, filtered, the filtrate basified with 13 ml 10 N sodium hydroxide and extracted with 100 ml ethyl acetate. The organic phase is dried, concentrated and the solid residue obtained is stirred for 48 h with 100 ml diethyl ether. After filtration the crude product is cleaned up by column chromatography (silica gel/dichloromethane) and recrystallized from 20 ml 2-propanol.

Provenance & Evidence