An approach to the synthesis of 4-phenyl-5-(arylimino)-Δ2-1,2,3,4-thiatriazolines was written by L’Abbe, Gerrit;Franek, Walter;Toppet, Suzanne;Delbeke, Pieter. And the article was included in Journal of Heterocyclic Chemistry in 1990.Reference of 1843-21-6 This article mentions the following:
4-Phenyl-5-arylimino-Δ2-1,2,3,4-thiatriazolines I (R = Ph, 4-MeC6H5) are presumably formed by reacting 5-arylaminothiatriazoles II with benzene at 50°, but decompose in situ to benzothiazole derivatives III. The reaction mechanism is discussed. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Reference of 1843-21-6).
N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Reference of 1843-21-6
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica