Recently, we developed a rapid procedure for the synthesis of substituted N-benzyl-N-methylformamides. Interestingly, in the reaction conducted on 4-chlorobenzaldehyde, a large amount of a by-product, N,N-di-(4-chlorobenzyl)-N-methylamine was produced with an isolated yield of 31.3%. N-(4-chlorobenzyl)-N-methylformamide was produced as the main product with an isolated yield of 52.0%. We hypothesized that the reaction conducted with N-ethylformamide may produce slightly higher yield of the by-product, N,N-di-(4-chlorobenzyl)-N-ethylamine as well as slightly lower yield of the main product, N-(4-chlorobenzyl)-N-ethylformamide. The reaction was conducted on 10 mmol scale at 178-181 °C. Column chromatography was used for the isolation of the products of the reaction. NMR-spectroscopy and elemental analysis were used to determine the structures of the products. The reaction was fully completed in 15 minutes and produced N-(4-chlorobenzyl)-N-ethylformamide as the main product with an isolated yield of 41.6%. N,N-di-(4-chlorobenzyl)-N-ethylamine was produced as the main by-product with an isolated yield of 34.0%. The reaction comprises a new rapid method for the synthesis of N-(4-chlorobenzyl)-N-ethylformamide. Research reported in this publication was supported by an Institutional Development Award (IDeA) from the National Institute of General Medical Sciences of the National Institutes of Health under grant number P20GM103442.

Rapid synthesis of N-(4-chlorobenzyl)-N-ethylformamide

251st National Meeting (2016)

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