SONOMA STATE UNIVERSITY

Chemistry 336 - Dale Trowbridge

Synthesis of a Sulfanilamide

References: Modern Experimental Organic Chemistry 4th Ed., Roberts, Gilbert, Rodewald and Wingrove

Hornback, Organic Chemistry, p715

Step 1 - Preparation and Purification of Acetanilide

Dissolve 0.10 mole of aniline (caution: aniline is toxic and can be absorbed through the skin) in a solution containing 9 ml of concentrated hydrochloric acid in 250 ml of deionized water using a 500 ml Erlenmeyer flask for the procedure. Swirl the mixture to aid in dissolving the aniline, and then add about 1 gram of decolorizing carbon. Carefully filter the mixture to remove the charcoal. The solution should now be clear and colorless

While this anilinium hydrochloride solution is being filtered to remove the decolorizing carbon, prepare a solution of sodium acetate trihydrate by dissolving 0.12 mole of CH₃CO₂Na^.3H₂O in 50 ml of water. To the filtered anilinium chloride solution add 0.25 mole of acetic anhydride followed immediately by the sodium acetate solution. Mix the reactants thoroughly by swirling, and then cool the mixture in an ice bath. Stir the cold solution vigorously as the product forms and crystallizes in the flask. Collect the product by vacuum filtration, wash with cold water and allow the product to dry in your locker for use in the preparation your assigned sulfanilamides.

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