Recently, we developed a rapid procedure for the synthesis of substituted N-benzylformamides. We also found that the reaction typically produces three minor byproducts, specifically, substituted N,N-dibenzylformamides, substituted N,N,N-tribenzylamines, and substituted N,N’-benzylidene-bis-formamides. It was interesting to investigate if the procedure could be modified towards the selective production of any of these by-products. We hypothesized that using oxalic acid as a catalyst may lead to a selective production of substituted N,N’-benzylidene-bis-formamides. In this work the hypothesis was tested by conducting the reaction on 4-chlorobenzaldehyde. The reaction was conducted on 10 mmol scale at 133ºC. NMR-spectroscopy and elemental analysis were used to determine the structure of the products. The reaction was fully completed in 1 minute and produced N,N’-(4-chlorobenzylidene)-bis-formamide as the main product with the isolated yield of 67.4%. The reaction provides a new rapid method for the synthesis of N,N’-(4-chlorobenzylidene)-bis-formamide. 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,N’-(4-chlorobenzylidene)-bis-formamide

249th National Meeting (2015)

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