8932. N-Sulfanilyl-3,4-xylamide

Nomenclature

CAS number: 120-34-3
N-[(-4-Aminophenyl)sulfonyl]-3,4-dimethylbenzamide; N1-(3,4-dimethylbenzoyl)sulfanilamide; Geigy 867; Irgafen.
C15H16N2O3S; mol wt 304.36.
C 59.19%, H 5.30%, N 9.20%, O 15.77%, S 10.54%.

Description and references

Prepd from p-nitrobenzenesulfonamide and 3,4-dimethylbenzoyl chloride; the resulting p-nitro-N-(3,4-dimethylbenzoyl)benzenesulfonamide is reduced with Fe and dil AcOH: Martin et al., US 2383874 (1945).

Chemical structure

Properties

Needles from alcohol, mp 222-223°. Sparingly sol in water. Marketed as the water-soluble sodium salt for making solns; a 5% aq soln having a pH of 8.2.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); Sulfonamides