Sulfonamides

Synthesis of Prontosil
SO2NH2

SO2NH2
NH2

N
N
N2+Cl- NH2
NH2
Dizotized sulfonamide m-phenylenediamine

NH2

Prontosil
Prontosil may be prepared by the diazotization of
sulphanilamide and subsequent reaction with m-
phenylene-diamine
Sulphapyridine
• It was used as the first specific drug for the treatment of pneumonia.
• However, due to its toxic nature, it has been replaced by less toxic
sulpha drugs and antibiotics.
• It is now used for the treatment of certain types of dermatitis.
Synthesis of Sulphapyridine
NH2
NHCOCH3

NHCOCH3
NH2

N HCl
O2S O2S
NH NH

SO2Cl
N N
4-acetylaminobenzene
sulfonyl chloride 2-aminopyridine
Intermediate
Sulphapyridine

• The reaction between 4-acetylamino benzene sulfonyl chloride and

2-aminopyridine gives on intermediate
• The acid hydrolysis of this intermediate results in the formation of
sulphapyridine
Sulfafurazole/Sulfisoxazole
• It is effective in treating infections caused by streptococci, gonococci, 
pneumococci, staphylococci, and also colon bacillus.
• About 90% of it binds with proteins in the plasma after oral
administration, and it diffuses mostly to tissues and tissue fluids,
which makes it the drug of choice for many systemic infections.
• Synonyms of this drug are gantrisin, fultrxin, sulfazin, sulfolar.
 Synthesis of Sulfisoxazole/Sulfafurazole
4-acetylamino
Benzene sulfonyl chloride

(intermediate)
3,4-dimethyl-5-amino
isoxazole

• The reaction between 3,4-dimethyl-5-amino isoxazole

and 4-acetlamino benezene sulfonyl chloride yields
an intermediate Sulfisoxazole
• The subsequent acid hydrolysis of this intermediate
results in the formation of isoxazole