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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis and properties of 2,4-diaminothiazoles》. Authors are Davies, W.; Maclaren, J. A.; Wilkinson, L. R..The article about the compound:Thiazole-2,4-diamine hydrochloridecas:72792-54-2,SMILESS:NC1=NC(N)=CS1.[H]Cl).Application In Synthesis of Thiazole-2,4-diamine hydrochloride. Through the article, more information about this compound (cas:72792-54-2) is conveyed.
CS(NH2)2 (I) and ClCH2CN (1 mol. each) in 15 parts MeOH, kept 3 weeks at room temperature or 1 week at 35°, give a nearly quant. yield of 2,4-diaminothiazole (II) HCl salt (III), m. above 360°; EtOH can be used as the solvent [a good yield of III results on refluxing 4 hrs.]; with Me2CO as the solvent, an oil gradually seps. and slowly crystallizes, yielding III; with N NaOH III yields II, m. 143° (decomposition). II yields a picrate, m. 233° (decomposition) (Land, et al., C.A. 41, 412i, gave above 350°). III (3.4 g.) in 10 cc. H2O, treated with 8 cc. 10% NaOH and then with 4 cc. Ac2O, gives 58% of 2,4-diacetamidothiazole, m. 240-1°, unchanged by boiling Ac2O in C5H5N, does not form a picrate. I and PhCHBrCN in EtOH (6 days at 35° or 6 hrs. on the water bath) give 83% of the HBr salt (IV), m. above 250° (decomposition), of 2,4-diamino-5-phenylthiazole (V), m. 163-4° (decomposition); picrate, yellow, m. 189-91° (decomposition). IV (2.7 g.), warmed with 1 cc. C5H5N, cooled, and treated with 10 cc. Ac2O (6 days at room temperature), gives 69% of the 2,4-di-Ac derivative (VI)of V, m. 233-4° [picrate (VII), yellow, m. 203-7° (decomposition)]. IV (5.4 g.), 2 cc. C5H5N, and 20 cc. Ac2O, refluxed 1 hr., give 92% 2,4-diacetamido-3-acetyl-5-phenylthiazole (VIII), m. 193-4.5°; VIII results on refluxing VI 1 hr. in Ac2O; refluxed 6 hrs. in 20% EtOH or treated 12 hrs. at room temperature with EtOH containing 0.33 ml. 10% NaOH, VIII yields VI; alc. picric acid gives VII. I (3.8 g.) and 4.5 g. MeCHClCN in 50 cc. 96% EtOH, kept 10 weeks at 40°, give 51% 2,4-diamino-5-methylthiazole (IX) HCl salt (X), m. 229-31° (decomposition); X results in 40% yield by refluxing the reactant 20 hrs. in EtOH. Mol. quantities of I, MeCHClCN, and NaI in EtOH, 3 months at room temperature, give 75% of the HI salt (XI) of IX, cream, m. 225° (decomposition); the yield is 72% on boiling the solution 10 hrs. X or XI with NaOH or NH4OH gives 2-amino-4-hydroxy-5-methylthiazole, m. 207-8° (decomposition); this results also on refluxing I and MeCHClCONH2 9 hrs. in EtOH. X is unchanged on heating with concentrated HCl on the water bath; 14 N H2SO4 gives an alkali-soluble oil (probably 2,4-dihydroxy-5-methylthiazole). IX picrate, orange, m. 216-17°; di-Ac derivative of IX, m. 23°. I and Me2CBrCN [MeCH(CN)CH2Cl] do not react on refluxing 13 hrs. in EtOH; PhNHCSNH2 and ClCH2CN, refluxed 1 hr. and kept 3 weeks at room temperature, give a small quantity of 4-hydroxy-2-anilinothiazole. CO(NH2)2 does not react with ClCH2CN (1 month at room temperature or refluxed 16 hrs.). CSe(NH2)2 (1.3 g.) and 0.7 g. ClCH2CN in 20 cc. EtOH, refluxed 2.5 hrs., give 0.8 g. 2,4-diaminoselenazole-HCl, does not m. at 250°, slowly deposits Se from hot aqueous-alc. solution; picrate, golden, m. 220-5°. III (0.5 g.) in 7.5 cc. H2O, refluxed 6 hrs., give 85% 2-amino-4-hydroxythiazole, m. 230-40° (decomposition); 1.5 g. III, 10 cc. H2O, and 5 cc. concentrated HCl, refluxed 5 hrs., give 2,4-dihydroxythiazole (XII). IV (5% aqueous solution), refluxed 3 hrs., gives 2-amino-4-hydroxy-5-phenyl thiazole, m. 229-30° [also formed (58% yield) from 5.6 g. PhCHBrCONH2 and 1.5 g. I in 50 cc. boiling EtOH (2.5 hrs.)]; picrate, m. 204°. Prepared in a similar manner to XII, but refluxed only 2 hrs., 2,4-dihydroxy-5-phenylthiazole m. 130-1°; it results also on refluxing 1 g. VI or VIII with 10 cc. 6 N HCl. H2NCS2NH4 (1.5 g.) and 2.2 g. PhNHCO2Et in 20 cc. 75% EtOH, 1 month at 35-40°, give 0.1 g. 5-benzylidenerhodanine, m. 203-4°; however, ClCH2CN gives only NH4Cl and S-containing indefinite liquids, which are also obtained with MeCSNH2, H2NCS2CH2Ph, or H2NCSNHCH2CH:CH2. V is a very potent analeptic but IX is without action.
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Reference:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics