Hydrochloric Acid → N1-hexanoylsulfanilamide

Participants

Reaction Steps

N4 -acetyl-N1 -hexanoylsulfanilamide from the previous step was treated with sodium hydroxide (24.6 g) in D.I. water (200 mL) while heating to reflux. After 3 hours reaction time, the heating was stopped and the solution pH adjusted to 8 with 2N HCl. The solution was cooled in an ice bath and then filtered to remove sulfanilamide. The filtrate was acidified with aqueous HCl to pH 2 to precipitate the product, N1 -hexanoylsulfanilamide, 37.9 g. This material was recrystallized from hot ethanol (75 mL) and precipitated by addition of 40 mL D.I. water to afford recrystallized N1 -hexanoylsulfanilamide, 24.8 g (43% overall yield). H1 -NMR indicated a purity >90%.

Provenance & Evidence