Journal of Organic Chemistry 2011-03-18

A synthesis of acetamidines.

Jitendra R Harjani, Chen Liang, Philip G Jessop

Index: J. Org. Chem. 76(6) , 1683-91, (2011)

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Abstract

The condensation of primary amine with N,N-dimethylacetamide dimethyl acetal yields a mixture of acetamidine and imidate ester. The product distribution in this reaction depends on the temperature, solvent, and structure of the primary amine. It is possible to suppress the formation of imidate ester by performing the reaction in the presence of excess dimethyl amine, yielding acetamidine as the exclusive product. For acetamidines that cannot be purified either by crystallization or distillation, this new method is necessary for the generation of pure acetamidines in good yields.