Lyashchuk, S. N.; Enya, V. I.; Doroshenko, T. F.; Skrypnik, Yu. G. published the artcile< Study of reaction routes in sulfonation of 2-aminothiazoles with chlorosulfonic acid>, HPLC of Formula: 57493-24-0, the main research area is thiazole amine sulfonation thermal isomerization thiazolesulfonic thiazolesulfamic acid preparation; charge distribution thiazole amine AM1 calculation sulfonation mechanism.
The sulfonation of 4-substituted 2-aminothiazoles with chlorosulfonic acid under mild conditions afforded primarily C-sulfonation product, 2-amino-5-thiazolesulfonic acids, which undergo thermal isomerization by heating in sulfuric acid into the corresponding stable 2-thiazolesulfamic acids. Reaction of 4-R-thiazole-2-amines (9-12) with ClSO3H gave 2-amino-4-R-thiazole-5-sulfonic acids (1-4; R = Me, 4-BrC6H4, 3-O2NC6H4, 4-ClC6H4); heating of 1-4 at 110° in concentrate H2SO4 gave 4-R-thiazole-2-sulfamic acids (5-8). Quantum chem. calculations at AM1 level revealed the presence of considerable neg. charge on the C-5 atom of the thiazole ring of 9-12, which accounts for the opposite sulfonation patterns for the aminothiazoles and aniline.
Russian Journal of Organic Chemistry published new progress about AM1 (molecular orbital method). 57493-24-0 belongs to class thiazole, and the molecular formula is C9H7N3O2S, HPLC of Formula: 57493-24-0.
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica