The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《5-(p-Aminobenzenesulfonamido)thiazole》. Authors are Arnold, M. H. M.; Scaife, C. W..The article about the compound:5-Aminothiazole-2-carbonitrilecas:860182-74-7,SMILESS:N#CC1=NC=C(N)S1).COA of Formula: C4H3N3S. Through the article, more information about this compound (cas:860182-74-7) is conveyed.
5-Amino-2-thiazolethiocarboxamide (I) (chrysean of Wallach, Ber. 7, 902(1874)), m. 204° (decomposition), results in 25-g. yield by passing H2S (20-30 l./hr.) into saturated aqueous NaCN and a little NH4OH for 3-4 hrs.; acidification of the filtrate gives 30-40% (of the NaCN) of a reddish brown precipitate which decomposes on heating with H2O to give H2S and a black alkali-soluble tar. Many other methods were tried with yields not over 15-20%. I (10 g.) and 23.9 g. Pb(OAc)2 in 70 ml. H2O, refluxed 3 hrs., give 5-amino-2-thiazolecarbonitrile (II), m. 103° (Hellsing, Ber. 32, 1497(1899)). If the filtrate containing II is treated with CaCO3 in slight excess above that required to neutralize the AcOH and the mixture is refluxed 2 hrs., there results a good yield of 5-amino-2-thiazolecarboxamide, decomposes 156°. Hydrolysis of II with dilute HCl gives a small yield of 2-amino-2-thiazolecarboxylic acid, decomposes 185°; this could not be decarboxylated to 5-aminothiazole. II and BzH in EtOH give the 5-benzylideneamino compound, light yellow, m. 141°; this and the benzylidene derivative of I are too easily hydrolyzed for this method of protecting the NH2 group to be of any use. Attempts to diazotize I and II in the normal way gave highly colored tars, which appeared to be formed by intermol. condensation; II is diazotized by gradual addition of the solution to excess of HCl and NaNO2 at 0°; I has been diazotized by adding its solution in C5H5N to excess of NOCl in C6H6. I and p-O2NC6H4SO2Cl in C5H5N give the 5-(p-nitrophenylsulfonamido) compound, m. 185° (decomposition); the same derivative of II m. 148°. p-AcNHC6H4SO2Cl and I in C5H5N give the 5-(p-acetamidophenylsulfonamido) compound (III), m., 253-5° (decomposition); shaking with PbCO3 and refluxing the filtrate for 3 hrs. give a moderately good yield of 5-sulfanilamidothiazole (IV), m. 185° (decomposition). III is completely inactive against streptococcal infections and IV, although active, has no advantage over established sulfonamide drugs.
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Reference:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics