Programing a cyanide-free transformation of aldehydes to nitriles and one-pot synthesis of amides through tandem chemo-enzymatic cascades was written by Zheng, Haoteng;Xiao, Qinjie;Mao, Feiying;Wang, Anming;Li, Mu;Wang, Qiuyan;Zhang, Pengfei;Pei, Xiaolin. And the article was included in RSC Advances in 2022.Synthetic Route of C6H5NS This article mentions the following:
In this work, a greener chemo-enzymic cascade to synthesize alky and aryl nitriles RCN (R = Ph, Bn, pentyl, furan-2-yl, etc.) from readily accessible aldehydes RCHO, that were further transformed into corresponding amides RC(O)NH2 via an artificial enzyme cascade was reported. A biphasic reaction system was designed to bridge chem. synthesis and enzymic catalysis through simple phase separation The biphasic system mainly perfectly avoided the inactivation of hydroxylamine on aldoxime dehydratase from Pseudomonas putida (OxdF1) and nitrile hydratase from Aurantimonas manganoxydans ATCC BAA-1229 (NHase1229). For the synthesis of various nitriles, moderate isolation yields of approx. 60% were obtained by the chemo-enzymic cascade. Interestingly, two seemingly conflicting reactions of dehydration and hydration were sequentially proceeded to synthesize amides by the synergistic catalysis of OxdF1 and NHase1229 in E. coli cells. An isolation yield of approx. 62% was achieved for benzamide at the one-liter scale. In addition, the shuttle transport of substrates and products between two phases is convenient for the product separation and n-hexane recycling. Thus, the chemo-enzymic cascade shows a potential application in the cyanide-free and large-scale synthesis of nitriles and amides. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Synthetic Route of C6H5NS).
3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Synthetic Route of C6H5NS
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts