9309. Thiazolsulfone

Nomenclature

CAS number: 473-30-3
5-[(4-Aminophenyl)sulfonyl]-2-thiazolamine; 2-amino-5-sulfanilylthiazole; 4-aminophenyl-2′-aminothiazolyl-5′-sulfone; thiazosulfone; thiazolesulfone; Promizole (Parke-Davis).
C9H9N3O2S2; mol wt 255.32.
C 42.34%, H 3.55%, N 16.46%, O 12.53%, S 25.12%.

Description and references

Prepd from the reaction products of p-nitrobenzenesulfonyl chloride and 2 mols of 2-aminothiazole: Bambas, J. Am. Chem. Soc. 67, 671 (1945); Bambas, US 2389126 (1945 to Parke, Davis).

Chemical structure

Properties

Fine needles from alc, mp 219-221° (some decompn). Sol in water at pH 6.5 to the extent of 30-40 mg per 100 ml at 28-30°. Freely sol in acetone, dioxane, 70% alc, dil acids. Moderately sol in abs alcohol, ethyl acetate and ether. It is a very weak acid, dissolves in 10% alkali (decompn) and forms an alkali metal salt at pH 10.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); Sulfones