4-Aminobenzenesulfonyl chloride

Sulfacetamide Sulfacetamide, iV -acetylsulfanilamide (33.1.44), is synthesized either by direct alkylation of acetamide with 4-aminobenzenesulfonyl chloride, or by reacting 4-aminobenzenesulfonamide with acetic anhydride and subsequent selective, reductive deacylation of the resulting acetamide 33.1.45 using a system of zinc-sodium hydroxide [37,38],... 

Closely related sulfoquinonimine species, e.g. 11 (R = H) and 12, have been suggested as arising from 4-aminobenzenesulfonyl chloride and certain derivatives58. Related to these... 

Write the structure of the material containing sulfonamide linkages that might be obtained upon polymerization of 4-aminobenzenesulfonyl chloride. 

Aminobenzenesulfonic acid and 3-aminobenzenesulfonyl chloride failed to react with EMME (77JMC1001). (Substituted phenylamino)meth-ylenemalonates (48) were prepared in the reaction of 2-(5-amino-2-alkoxyphenyl)-8-azapurin-6-ones and EMME at 140°C (78GEP2747199 82SZP627755). 

The 1,2,5-benzothiadiazepine (543 R = H) has been prepared by cyclizing the condensation product of 2-aminobenzenesulfonyl chloride and 2-aminoacetic acid. 

We can now see several reasons for first protecting the reactive amino group on the aniline molecule. First, to attempt the introduction of the sulfonyl group directly on aniline would very fikely lead to a species (p-aminobenzenesulfonyl chloride) that would react with itself (act as a di-fonctional monomer) to produce a sulfonamide polymer ... 

Bromo-3-hydroxy-5,6-dimethylpyrazine and 2-bromo-5-hydroxy-3,6-diphenyl-pyrazine with phosphoryl chloride afforded 2,3-dichloro-5,6-dimethylpyrazine and 2,5-dichloro-3,6-diphenylpyrazine, respectively (817) and the bromo substituent in 2-amino-3-bromo-5,6-dimethylpyrazine and its p-aminobenzenesulfonyl derivative have been replaced by chlorine on treatment with aqueous hydrochloric acid in ethanol (812). 

---