Structure of sulfonic acids of 2-amino-4-methylthiazole was written by Postovskii, I. Ya.;Mamykina, T. S.. And the article was included in Zhurnal Obshchei Khimii in 1953.Name: 2-Acetamido-4-methylthiazole-5-sulfonyl chloride This article mentions the following:
Ochiai and Nagasawa, C.A. 33, 7782.9; Hurd, et al., C.A. 45, 155e. ClSO3H with 2-acetamido-4-methylthiazole (I) yields 2-acetamido-4-methyl-5-thiazolesulfonyl chloride (II). The structures proposed by Hurd and Ochiai (loc. cit.) are erroneous. The acid (III), m. 253-6°, formed by hydrolysis of II and on heating with H2SO4 changes to an acid, decomposing above 340°, an example of an unusual transition of the sulfonic acid into a sulfamic acid (IV or IVa). Addition of ClSO3H to I in CCl4 gives some 40% pure III, m. 256° (decomposition). The following technique gives better results. I (17.5 g.) in 75 ml. CCl4 was slowly added with cooling over 3 hrs. to 22 ml. ClSO3H (temperature kept under 14°), and the mixture poured on ice, yielding 79% III, decompose 253-6° (from H2O). I (20 g.) added to 30 ml. concentrated H2SO4, and the mixture heated 5 hrs. at 150-65°, cooled to 50°, and poured into ice water gave 76% IV (or IVa), m. above 350° (from H2O). III taken up in aqueous NaOH, the solution evaporated, and the resulting Na salt (7.7 g.) treated with 17 ml. Ac2O, refluxed 2 hrs., and cooled gave 8.8 g. Ac derivative, which, heated 1-1.5 hrs. with 15 g. PCl5 on a steam bath, cooled, and treated with ice, gave II, m. 156-7° (from CCl2:CHCl), identical with the specimen obtained from ClSO3H and I directly. II also forms from ClSO3H and the Na salt of III, but the yield is lower. I contains 1 active H/(Zerevitinov) mol. II (2.5 g.) added to 1.2 g. EtNHPh in dry pyridine, kept 1 day, and diluted with H2O gave 91% of the corresponding N-ethylanilide, m. 188-9° (from dilute EtOH). This with Me2SO4 in N NaOH gave 74% methylated product, probably (V) or (VA), m. 128-9°, which does not react with MeMgI, indicating the absence of active H. Thus the ethylanilide must have structure (VI). II in dry pyridine treated with cooling with gaseous Me2NH gave 93% 2-acetamido-N,N,4-trimethyl-5-thiazolesulfonamide, m. 242-3° (from dilute EtOH), which has 1 active H, at the AcNH group. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Name: 2-Acetamido-4-methylthiazole-5-sulfonyl chloride).
2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Name: 2-Acetamido-4-methylthiazole-5-sulfonyl chloride
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica