Some derivatives of NN′-biscarboxymethyl- and NN′-bis-(β-carboxyethyl)-ethylenediamine

Abstract

The preparation of some new derivatives of NN′-biscarboxymethyl- and NN′-bis-(β-carboxyethyl)-ethylene-diamine [(VII) and (XVIII)] is described. The bis-amide of the latter compound on treatment with formaldehyde yielded 1,2-bis-(4-oxohexahydro-1-pyrimidyl)ethane (XXII). The bis-amide of the amino-acid (VII) was obtained in low yield from the corresponding NN′-dibenzyl bis-amide; direct preparation from (VII) was prevented by ready lactam formation in this series. When treated with potassium cyanate the amino-acids (VII) and (XVIII) gave, respectively, 1,2-bis-(2,4-dioxoimidazolidin-1-yl)ethane (XI) and 1,2-bis(2,4-dioxohexahydro-1-pyrimidyl)ethane (XXIII).