8934. Sulfaperine

Nomenclature

CAS number: 599-88-2
4-Amino-N-(5-methyl-2-pyrimidinyl)benzenesulfonamide; N1-(5-methyl-2-pyrimidinyl)sulfanilamide; 5-methyl-2-sulfanilamidopyrimidine; 2-sulfanilamido-5-methylpyrimidine; isosulfamerazine; 5-methylsulfadiazine; Pallidin (Merck KGaA); Retardon (Chassot); Rexulfa (Medici); Sintosulfa (Afi); Sulfatreis (Ecobi).
C11H12N4O2S; mol wt 264.30.
C 49.99%, H 4.58%, N 21.20%, O 12.11%, S 12.13%.

Description and references

Prepd by condensing 2-amino-5-methylpyrimidine with acetylsulfanilyl chloride followed by hydrolysis of the acetyl group with NaOH: Sprague, US 2407966 (1946 to Sharp & Dohme).

Chemical structure

Properties

Minute, cream-colored crystals, mp 262-263°. Very sparingly sol in water, ethanol; ≈40 mg/100 ml H2O at pH 5.5. Sol in aq solns of acids and alkalies. Forms a water-sol sodium salt.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); Sulfonamides