Skip to main content
Log in

Aminomethylation of Thiourea with Formaldehyde and Cyclic Amines

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

An Erratum to this article was published on 01 October 2018

This article has been updated

Abstract

Three-component condensation of thiourea with equimolar amounts of formaldehyde and morpholine afforded N-(morpholin-4-ylmethyl) derivative, whereas analogous reaction with 2 equiv of formaldehyde and amine gave symmetrical N,N′-bis(morpholin-4-ylmethyl)thiourea. In the condensation of thiourea with piperidine and formaldehyde, only symmetrical N,N′-bis(piperidin-1-ylmethyl)thiourea was isolated, regardless of the reactant ratio.

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

Change history

  • 14 December 2018

    Reference to the funding source is missing in the article:

    This study was performed in the framework of the project (no. 10.735.2014/K) and base parts (no. 10.7608.2017/8.9) of state assignment of the Ministry of Education and Science of the Russian Federation in the sphere of research activity.

References

  1. Mertschenk, B., Beck, F., and Bauer, W., Ullmann’s Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2000, 5th ed., vol. 36, p. 671.

    Google Scholar 

  2. Granik, V.G. and Grigor’ev, N.B., Russ. Chem. Bull., Int. Ed., 2002, vol. 51, no. 11, p. 1973.

    Article  CAS  Google Scholar 

  3. Proskuryakov, S.Ya., Konoplyannikov, A.G., Skvortsov, V.G., Mandrugin, A.A., and Fedoseev, V.M., Russ. Chem. Rev., 2005, vol. 74, no. 9, p. 859.

    Article  CAS  Google Scholar 

  4. Studentsov, E.P., Ramsh, S.M., Kazurova, N.G., Neporozhneva, O.V., Garabadzhiu, A.V., Kochina, T.A., Voronkov, M.G., Kuznetsov, V.A., and Krivorotov, D.V., Obz. Klin. Farmakol. Lek. Ter., 2013, vol. 11, no. 4, p. 3.

    Article  Google Scholar 

  5. Bögemann, M. and Zauker, E., German Patent no. 575 114, 1933; Chem. Abstr., 1933, vol. 27, p. 3483.

    Google Scholar 

  6. Böhme, H., Dietz, K., and Leidreiter, K.D., Arch. Pharm., 1954, vol. 287, p. 198.

    Article  Google Scholar 

  7. Singh, B., Mahajan, S., Sheikh, H.N., Sharma, M., and Kalsotra, B.L., Monatsh. Chem., 2012, vol. 143, no. 1, p. 91.

    Article  CAS  Google Scholar 

  8. Kalopissis, G., Aberg, J.-L., Ghilardi, G., and De Beaulieu, H.P., FRG Patent Appl. no. 1 803 688, 1969; Chem. Abstr., 1969, vol. 71, p. 73 956s.

    Google Scholar 

  9. Weaver, W.I., Simons, J.K., and Baldwin, W.E., J. Am. Chem. Soc., 1944, vol. 66, no. 2, p. 222.

    Article  CAS  Google Scholar 

  10. Silverstein, R.M., Webster, F.X., and Kiemle, D.J., The Spectrometric Identification of Organic Compounds, Hoboken: Wiley, 2005, 7th ed., p. 106.

    Google Scholar 

  11. Bogatskii, A.V., Luk’yanenko, N.G., and Kirichenko, T.I., Chem. Heterocycl. Compd., 1983, vol. 19, no. 6, p. 577.

    Article  Google Scholar 

  12. Truter, M.R., Acta Crystallogr., 1967, vol. 22, p. 556.

    Article  CAS  PubMed  Google Scholar 

  13. Pollak, F., Mod. Plast., 1939, vol. 16, no. 10, p. 74; Chem. Abstr., 1939, vol. 33, p. 62 497.

    Google Scholar 

  14. Schiavi, B., Ahond, A., Poupat, C., and Potier, P., Synth. Commun., 2002, vol. 32, no. 11, p. 1671.

    Article  CAS  Google Scholar 

  15. Burla, M.C., Caliandro, R., Carrozzini, B., Cascarano, G.L., Cuocci, C., Giacovazzo, C., Mallamo, M., Mazzone, A., and Polidori, G., J. Appl. Crystallogr., 2015, vol. 48, no. 1, p. 306.

    Article  CAS  Google Scholar 

  16. Macrae, C.F., Bruno, I.J., Chisholm, J.A., Edgington, P.A., McCabe, P., Pidcock, E., Rodrigues-Monge, L., Taylor, R., van de Streek, J., and Wood, P.A., J. Appl. Crystallogr., 2008, vol. 41, no. 2, p. 466.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yu. A. Martinovich.

Additional information

Original Russian Text © Yu.A. Martinovich, S.M. Ramsh, F. Hamoud, V.S. Fundamenskii, V.V. Gurzhii, V.I. Zakharov, E.S. Khrabrov, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 6, pp. 876–883.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Martinovich, Y.A., Ramsh, S.M., Hamoud, F. et al. Aminomethylation of Thiourea with Formaldehyde and Cyclic Amines. Russ J Org Chem 54, 878–885 (2018). https://doi.org/10.1134/S107042801806009X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107042801806009X

Navigation