Sodium Carbonate → 4,9-Dioxo-2,5,8,11-tetra-azabicyclo[10,4,0]-hexadecane

Participants

Reaction Steps

Sodium carbonate (226 g., 2.13 mol.) and trans-1,2-diaminocyclohexane (14.1 ml., 117 mmol.) were added to a solution of N,N'-dichloroacetylethylenediamine (25 g., 117 mmol.) in dry acetonitrile (3.75 l.) under nitrogen. N,N'-dichloroacetylethylenediamine was prepared as reported by Lin W.C., Fiqueira, J. A. D and Alt, H. G. in "New multidentate potential inophors of ether-amide type", Monat. Chem., 1985, 116, 217-221. The reaction mixture was refluxed for 20 hours. The insoluble material formed was filtered off and the volume of the filtrate was reduced to 1 l. by evaporation. Crystals of the compound (A) slowly formed at room temperature. They were collected by filtration and the product was purified by crystallization in acetonitrile. The yield was 7.43 g. of a white solid.

Provenance & Evidence