Chloride → N-carbobenzyloxy-4-(4,14-pentadecadienylamino)benzoyl chloride

Participants

Reaction Conditions

Reaction Steps

To 15 g. of 4-(4,14-pentadecadienylamino)benzoic acid in 200 mml. warm chloroform is added 15 g. sodium carbonate in 150 ml. water. To the vigorously stirred mixture is added 10 g. carbobenzoyl chloride. After 2 hours stirring at 40° C., the layers are separated, the chloroform layer is washed three times with 1N hydrochloric acid, dried, and the solvent evaporated to yield an oil. The oil is dissolved in 300 ml. toluene, treated with 15 ml. of thionyl chloride, and the solution is refluxed for 5 hours. The solvents are evaporated and the residue is dissolved three times in toluene, evaporating each time to yield a viscous, orange oil.

Provenance & Evidence