Reaction of α-bromobenzyl cyanide with ethyl xanthamidate (thioncarbamate) was written by Davies, W.;Maclaren, J. A.. And the article was included in Journal of the Chemical Society in 1951.Application In Synthesis of 4,5-Diphenylthiazol-2-amine This article mentions the following:
Bu xanthamidate, b15 127-30°, m. 16-19°, 45%. Equimol. quantities of PhCHBrCN (I) and EtOCSNH2 (II) in EtOH, refluxed 3 hrs., give [PhC(CN):]2 and EtSCONH2; the same products result on keeping the solution 5 days at 40°. I and II in C6H6, refluxed 3 hrs., give α-carbamylthiobenzyl cyanide (III), m. 105-6°; this results also when I and II are kept 10 days at 40°. III (0.5 g.) in 5 ml. EtOH and 5 ml. concentrated HCl, refluxed 2 hrs., give 2, 4-dihydroxy-5-phenylthiazole; 0.5 g. III in 15 ml. EtOH containing 0.05 g. Na, kept 2 days at room temperature, gives 0.2 g. [PhC(CN):]2. III (0.5 g.) and 0.7 g. HgCl2 in 5 ml. EtOH and 30 ml. H2O, heated to boiling, give the Hg salt (C16H12N2S2Hg), m. 159-60°, of PhCH(SH)CN. MeSCONH2 and HgCl2 in hot H2O give chloromercurithiolmethane, m. above 300°. III and PhNH2 on heating evolve NH3 and yield CO(NHPh)2; p-MeOC6H4NH2 gives CO(NHC6H4OMe-p)2. II (10.5 g.), 40 ml. 60% I (in PhCH2CN), and 18 g. AcONa in 60 ml. C6H6, refluxed 5 hrs., give 10% 2, 5-bis(2-ethoxy-5-phenyl-4-thiazolylimino)-3, 4-diphenylpyrroline (IV), red, m. 222.5-3°; with concentrated HCl in boiling AcOH IV yields 68% 2, 4-dihydroxyphenylthiazole and 99% diphenylmaleic imide. The 2-MeO analog of IV, red, m. 277-8°, 12%; the 2-BuO analog, red, m. 205-5.5°, 11%. Test tube experiments showed that compounds containing the C(:NH)N: group gives colored compounds but the pigments could not be isolated because of the simultaneous formation of tars. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Application In Synthesis of 4,5-Diphenylthiazol-2-amine).
4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Application In Synthesis of 4,5-Diphenylthiazol-2-amine
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica