Synthesis of 5-Phenylthiazolamines by Using Thiourea as an α-Bromination Shuttle was written by Roslan, Irwan Iskandar;Ng, Kian-Hong;Chuah, Gaik-Khuan;Jaenicke, Stephan. And the article was included in European Journal of Organic Chemistry in 2017.Electric Literature of C15H12N2S This article mentions the following:
A straightforward synthesis of 5-phenylthiazolamines by coupling thiourea with phenylacetones, phenylacetophenones, and β-tetralone has been developed. Thiourea acts as a substrate and an α-bromination shuttle by transferring a Br atom from CBrCl3 to the α-carbon of the carbonyl moiety. A series of steps are then triggered to reach the final product. Isolated yields from 80 to 95 % were obtained. Key features of this protocol include its minimal use of reagents (i.e., substrates, CBrCl3, and CsHCO3), its short reaction times under mild conditions (at 80 °C for 2-3 h), and its ease of scale up to prepare gram quantities of product. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Electric Literature of C15H12N2S).
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. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Electric Literature of C15H12N2S
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica