P-Acetamidobenzenesulfonamide

The replacement of the reactive 5-chloro by a sulfonamido group in 1,2,4-thiadiazoles affords a convenient synthesis of the 5-sulfonamido heterocycles.92- 3,168-172 173 Thus, 5-halogeno compounds (171), on treatment with p-acetamidobenzenesulfonamide and potassium carbonate in diphenyl ether at 200°, afford the sulfonamido derivatives (170) in 70 % yields. Nitrobenzenesulfonamides do not react. This route is valuable, because the products are obtainable with difficulty by sulfonylation of the parent amine (see Section III,D, 1,A).8-8S-86-87 The superiority of route 171 -> 170 over route 169-y 170, though unusual in the heterocyclic field, recalls similar observations made in the synthesis of sulfonamidotriazines.174... 

In this experiment, you will prepare the sulfa drug sulfanilamide by the following synthetic scheme. The synthesis involves converting acetanilide to the intermediate p-acetamidobenzenesulfonyl chloride in Step 1. This intermediate is converted to sulfanilamide by way of p-acetamidobenzenesulfonamide in Step 2. 

Brown, Mueller, and Morehouse reported studies with 2-chloro-4-nitrobenzamide (XIV) and combinations of XIV with N-(p-nitro-phenyl)-4-acetamidobenzenesulfonamide (XV) against coccidiosis. These authors noted that tolerated levels of XIV were able to protect chickens from mortality due to exposure to E. necatrix or E. tenella, but that protection against E. acervulina could be achTeved only at toxic levels with XIV alone. A combination equivalent to a final dietary concentration of 0.025% of XIV and 0.020% of XV, designated Novastat prevented development of coccidiosis when tested against all three Eimeria species E. tenella,... 

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