Oxalic Acid → N-(2-fluorophenyl)-1-pyrrolidinecarboximidamide

Participants

Reaction Steps

To stirred solution of 2.0 g (0.006 mol) of N-(2-fluorophenyl)-S-methylisothiourea in 50 ml of ethanol was added 2.0 g (0.028 mol) of pyrrolidine and the reaction refluxed for eight hours. The solvent was then evaporated and to the residue was added 100 ml of water and 20 ml of 2 N sodium hydroxide. The aqueous phase was then extracted with ethyl acetate (3×100 ml) and the organic phase dried over magnesium sulphate. Evaporation of the solvent gave a crude residue. This crude residue was then dissolved in 25 ml of hot isopropanol and oxalic acid was added in excess. Upon cooling a white solid crystallized and was collected by filtration and dried at 60° C. for 24 hours to give the oxalate salt of N-(2-fluorophenyl)-1-pyrrolidinecarboximidamide, M.P. 172-173° C.

Provenance & Evidence