8897. Sulfabenzamide

Nomenclature

CAS number: 127-71-9
N-[(4-Aminophenyl)sulfonyl]benzamide; N-sulfanilylbenzamide; N1-benzoylsulfanilamide; N-(p-aminobenzenesulfonyl)benzamide; Sulfabenzide.
C13H12N2O3S; mol wt 276.31.
C 56.51%, H 4.38%, N 10.14%, O 17.37%, S 11.60%.

Description and references

Prepn: Crossley et al., J. Am. Chem. Soc. 61, 2950 (1939); Dvornikoff, US 2240496 (1941 to Monsanto); GB 541958 (1942 to Schering AG); Siebenmann, Schnitzer, J. Am. Chem. Soc. 65, 2126 (1943).

Chemical structure

Properties

Long, hexagonal prisms from 60% alcohol, mp 181.2-182.3°. pKa (25°): 4.57. Substantially insol in water. One gram dissolves in 3225 ml of water at 30°, in 33 ml of 95% ethanol, in 9 ml of acetone. Soly in 1N NaOH or KOH: ≈16 g/100 ml; pH just above 7.0. Aq solns of the water-soluble sodium salt have the same pH.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antimicrobial.

Keywords

Antibacterial (Synthetic); Sulfonamides