8904. Sulfadicramide

Nomenclature

CAS number: 115-68-4
N-[(4-Aminophenyl)sulfonyl]-3-methyl-2-butenamide; 3-methyl-N-sulfanilylcrotonamide; N1-senecioylsulfanilamide; N-sulfanilylseneciamide; N1-dimethylacroylsulfanilamide; N-sulfanilyl-β,β-dimethylacrylamide; Irgamide (Dispersa).
C11H14N2O3S; mol wt 254.31.
C 51.95%, H 5.55%, N 11.02%, O 18.87%, S 12.61%.

Description and references

Prepd from β,β-dimethylacrylamide by treatment with sodamide and p-nitrobenzenesulfonyl chloride; the resulting 4-nitro-N-(β,β-dimethylacrylyl)benzenesulfonamide is reduced with Fe and dil AcOH: Martin, Hfliger, US 2417005 (1947), cf. US 2383874 (1945).

Chemical structure

Properties

Crystals from alc. mp 184-185°. Slightly sol in water, ether. Freely sol in alcohol, acetone. For the prepn of solns the water-soluble sodium salt is marketed. A 20% aq soln of the sodium salt has a pH of 8.3.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); Sulfonamides