Skip to main content
Log in

1,3-Diacyl derivatives of imidazolidine and hexahydropyrimidine: I. Preparation by novel method and characterization

  • Technical
  • Published:
Journal of the American Oil Chemists’ Society

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Riebsomer, J.L., and G.H. Morey, J. Org. Chem. 15:245–248 (1950).

    Article  CAS  Google Scholar 

  2. Morey, G.H., U.S. Patent 2,535,747 (Commercial Solvents Corp.), December 26, 1950; Chem. Abstr. 45:3877 (1951).

  3. Senkus, M., J. Amer. Chem. Soc. 68:1611–1613 (1946).

    Article  CAS  Google Scholar 

  4. Hoffman, K., “Imidazole and its Derivatives,” Interscience Publishers Inc., New York, 1953, p. 242.

    Google Scholar 

  5. Billman, J.H., and L.C. Dorman, J. Med. Chem. 6:701–705 (1963).

    Article  CAS  Google Scholar 

  6. Stromberg, V.L., (Petrolite Corp.), U.S. Patent 2,888,458 (May 26, 1959); Chem. Abstr. 54:2375 (1960).

  7. Hughes, W.B., (Cities Service Research and Development Co.), U.S. Patent 2,836,558 (May 27, 1958); Chem. Abstr. 52:15045 (1958).

  8. 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).

    Google Scholar 

  9. 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).

    Google Scholar 

  10. Stromberg, V.L., (Petrolite Corp.), U.S. Patent 2,854,322 (Sept. 30, 1958); Chem. Abstr. 53:10263 (1959).

  11. Senkus, M., (Commercial Solvents Corp.), U.S. Patent 2,415,047 (Jan. 28, 1947); Chem. Abstr. 41:3252 (1947).

  12. Billman, J.H., and M.S. Khan, J. Med. Chem. 8:498–499 (1965).

    Article  CAS  Google Scholar 

  13. Billman, J.H., and M.S. Khan, Ibid. 9:347–351 (1966).

    Article  CAS  Google Scholar 

  14. Billman, J.H., and M.S. Khan, Ibid. 11:312–314 (1968).

    Article  CAS  Google Scholar 

  15. Vail, S.L., and C.M. Moran, (USDA) U.S. Patent 3,376,101 (April 2, 1968); Chem. Abstr. 68:106039 (1968).

    Google Scholar 

  16. Vail, S.L., and C.M. Moran, (USDA) U.S. Patent 3,341,550 (Sept. 12, 1967); Chem. Abstr. 67:100974 (1967).

    Google Scholar 

  17. Vail, S.L., R.H. Barker and C.M. Moran, J. Org. Chem. 31:1642–1644 (1966).

    Article  CAS  Google Scholar 

  18. Titherley, A.W., and G.E.K. Branch, J. Chem. Soc. 103:330–340 (1913).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

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

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02883764

Keywords

Navigation