Abstract
The reaction of formaldehyde and diamides of 1,2-diamines in acetic acid containing a trace of hydrochloric acid was found to give 1,3-diacyl derivatives of imidazolidine in high yield. The similar reaction of formaldehyde and diamides of 1,3-propylenediamine gave high yields of 1,3-diacylhexahydropyrimidines. Attempts to extend this reaction to other aldehydes than formaldehyde failed, as did attempts to condense formaldehyde with a diamide which would give a four-membered or seven-membered ring system, the diamide being recovered unchanged in each instance. Twenty-two new compounds were prepared and characterized.
Similar content being viewed by others
References
Riebsomer, J.L., and G.H. Morey, J. Org. Chem. 15:245–248 (1950).
Morey, G.H., U.S. Patent 2,535,747 (Commercial Solvents Corp.), December 26, 1950; Chem. Abstr. 45:3877 (1951).
Senkus, M., J. Amer. Chem. Soc. 68:1611–1613 (1946).
Hoffman, K., “Imidazole and its Derivatives,” Interscience Publishers Inc., New York, 1953, p. 242.
Billman, J.H., and L.C. Dorman, J. Med. Chem. 6:701–705 (1963).
Stromberg, V.L., (Petrolite Corp.), U.S. Patent 2,888,458 (May 26, 1959); Chem. Abstr. 54:2375 (1960).
Hughes, W.B., (Cities Service Research and Development Co.), U.S. Patent 2,836,558 (May 27, 1958); Chem. Abstr. 52:15045 (1958).
Van Hook, J.O., and W.E. Craig, (Rohm and Haas Co.), U.S. Patent 2,675,387 (April 13, 1954); Chem. Abstr. 49:4729 (1955).
Craig, W.E., and J.O. Van Hook, (Rohm and Haas Co.), U.S. Patent 2,675,381 (April 13, 1954); Chem. Abstr. 50:411 (1956).
Stromberg, V.L., (Petrolite Corp.), U.S. Patent 2,854,322 (Sept. 30, 1958); Chem. Abstr. 53:10263 (1959).
Senkus, M., (Commercial Solvents Corp.), U.S. Patent 2,415,047 (Jan. 28, 1947); Chem. Abstr. 41:3252 (1947).
Billman, J.H., and M.S. Khan, J. Med. Chem. 8:498–499 (1965).
Billman, J.H., and M.S. Khan, Ibid. 9:347–351 (1966).
Billman, J.H., and M.S. Khan, Ibid. 11:312–314 (1968).
Vail, S.L., and C.M. Moran, (USDA) U.S. Patent 3,376,101 (April 2, 1968); Chem. Abstr. 68:106039 (1968).
Vail, S.L., and C.M. Moran, (USDA) U.S. Patent 3,341,550 (Sept. 12, 1967); Chem. Abstr. 67:100974 (1967).
Vail, S.L., R.H. Barker and C.M. Moran, J. Org. Chem. 31:1642–1644 (1966).
Titherley, A.W., and G.E.K. Branch, J. Chem. Soc. 103:330–340 (1913).
Author information
Authors and Affiliations
About this article
Cite this article
Mod, R.R., Magne, F.C. & Sumrell, G. 1,3-Diacyl derivatives of imidazolidine and hexahydropyrimidine: I. Preparation by novel method and characterization. J. Am. Oil Chem. Soc. 48, 254–256 (1971). https://doi.org/10.1007/BF02883764
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02883764