Aziridine → N-cyano-N'-methyl-1-aziridinoamidine

Participants

Reaction Steps

N-Cyano-N'-methyl-O-phenylisourea (10.0 g, 0.0571 mol) was added in half-gram batches during 6 min to aziridine (7.926 g, 0.184 mol) cooled to 0° and stirred. A solution was formed, from which after 5 min a colourless solid crystallised out. The reaction mixture was stirred at 20° for 90 min. and then cooled to 0° to complete crystallisation. Filtration and washing the residue with cold ether gave crystalline N-cyano-N'-methyl-1-aziridinoamidine (4.09 g, 57%), m.p. 134°-135°, Rf 0.64-0.66 (silica, acetonitrile). Further product (1.78 g) was isolated from the ether washings, giving a total yield of 5.87 g, 82%.

Provenance & Evidence