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The mechanism of the reaction between amines with dimethyl carbonate (DMC) has been investigated. Whereas in the absence of bases, they give methylation and carboxymethylation reactions without selectivity (B Al 2 and B Ac 2 mechanisms, respectively), in the presence of bases, the B Ac 2 mechanism prevails. The carbamate already formed reacts further with DMC via the B Al 2 mechanism to give the corresponding  N -methyl derivative. Such pronounced double selectivity has been explained in terms of Pearson's Hard-Soft Acid-Base (HSAB) theory.

Direct synthesis of N-methylurethanes from primary amines with dimethyl carbonate