Schmidt reaction in ionic liquids: highly efficient and selective conversion of aromatic and heteroaromatic aldehydes to nitriles with [BMIM(SO3H)][OTf] as catalyst and [BMIM][PF6] as solvent was written by Nandi, Ganesh C.;Laali, Kenneth K.. And the article was included in Tetrahedron Letters in 2013.Name: 2-Cyanothiazole This article mentions the following:
A mild and selective method is presented for the conversion of aromatic and heteroaromatic aldehydes to nitriles via the Schmidt reaction with TMSN3 by using [BMIM(SO3H)][OTf] as catalyst and [BMIM][PF6] as solvent. E.g., in the presence of this catalyst in [BMIM][PF6], reaction of 2-MeOC6H4CHO with TMSN3 gave 100% 2-MeOC6H4CN. The method offers high yields and simple product isolation, and avoids the use of liquid superacids or corrosive Lewis acids commonly employed for this transformation. It also offers some potential for recycling/reuse of the IL solvent. In the experiment, the researchers used many compounds, for example, 2-Cyanothiazole (cas: 1452-16-0Name: 2-Cyanothiazole).
2-Cyanothiazole (cas: 1452-16-0) 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.Name: 2-Cyanothiazole
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica