Hydrochloric Acid → Pentyl 4-sulfamoylbenzoate

Participants

Reaction Steps

A slurry of 32.1 g (0.15 mole) of p-carboxybenzenesulfonamide, methyl ester in 400 ml of n-pentanol was treated with 25 g of anhydrous hydrogen chloride and the mixture was heated at reflux temperature for 4 hr. The reaction was again treated by the slow addition of anhydrous hydrogen chloride during 8 hr of slow distillation. Approximately 150 ml of distillate was collected. The distillate was replaced in the reaction mixture with 150 ml of n-pentanol and the solution was heated at reflux for 66 hr. Excess pentanol and hydrogen chloride were removed by distillation under vacuum. The residue wad crystallized from a mixture of 350 ml of ethyl acetate and 500 ml of petroleum ether to give 22.0 g (54%) of white flakes, mp 96°-98° C.

Provenance & Evidence