Citric Acid → HCID 70360585, compound

Participants

Reaction Steps

A mixture of 2.72 g (0.0235 mole) of N,N-diethylethylenediamine and 4.37 g (0.027 mole) of 1,1'-carbonyldiimidazole in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 5.11 g (0.0216 mole) of N,N-diethyl-N'-(2-phenoxyethyl)-1,2-ethanediamine in 50 ml of tetrahydrofuran was added, and the solution was refluxed for 20 hr. The solvent was removed in vacuo and the residue was dissolved in a mixture of 250 ml of diethyl ether and 250 ml of methylene chloride. The solution was extracted with several portions of water and was dried over magnesium sulfate. The solvent was removed in vacuo to give an oil. A solution of the oil in methanol was treated with a two-fold excess of citric acid, diethyl ether was added, and 12.22 g (74.2%) of the title compound crystallized as a white crystalline solid, m.p. 80°-85° C.

Provenance & Evidence