Chloride → N-carbobenzyloxy-4-(hexadecylamino)benzoyl chloride

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To 15 g. of 4-(hexadecylamino)benzoic acid in 200 ml. water chloroform is added 15 g. sodium carbonate in 150 ml. water. To the vigorously stirred solution is added 10 g. carbobenzoyl chloride. After 2 hours stirring at 40° C., the layers are separated, washed three times with 1N hydrochloric acid, dried, and evaporated to 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.

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