Chromatographic Separation of the Lyophilized Reaction Products of Formaldehyde and Methyl Carbamate

A mixture of the condensation products obtained from formaldehyde and methyl carbamate, prepared in an aqueous medium according to the procedure of Reid and coworkers, was studied and its components tentatively identified. The mixture was lyophilized, and birefringence under polarized light showed that the solid product was comprised of mixed crystals. These crystalline products were then separated as essentially pure compounds by thick-layer chro matography: mass spectra of the chromatographic eluates contained masses 279, 284, and 137 that appear to be molecular ions, and a mass of 129 that is possibly a fragment of a linear dimer.