Selective carbomethoxylation of aromatic diamines

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Abstract
The reactivity of industrially relevant amines, 4,4′-methylenedianiline (MDA) and 2,4-diaminotoluene (TDA), towards methylphenylcarbonate (MPC), in the presence of Ph2P(O)OH, has been investigated. Both MDA and TDA are catalytically and selectively converted into mono- and di-methylcarbamate esters. Under the relatively mild working conditions used, the formation of ureas and/or N-methyl derivatives is totally repressed. The full spectroscopic characterization of the compounds formed upon interaction of amines with Ph2P(O)OH is also reported. The methodology here described also holds for other mono- and di-amines, both aliphatic and aromatic.

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