Organic Chemistry II  | Lecture | Laboratory

Organic Chemistry Laboratory II
Synthesis and Activity of Sulfanilamide
Mechanisms for Reactions Used in the Synthesis of Sulfanilamide

Step 1:  Chlorosulfonic acid undergoes dimerization to generate the electrophilic reagent used to react with acetanilide

Step 2:  Chlorosulfonic anhydride reacts with acetanilide via and electrophilic aromatic substitution to generate p-acetamidobenzenesulfonylchloride.

Step 3:  p-Acetamidobenzenesulfonyl chloride reacts with ammonia to generate p-acetamidobenzenesulfonamide.

Step 4:  The amide group of p-acetamidobenzenesulfonamide is hydrolyzed in aqueous acid.