Ja M. I agree with Soumik De. In addition to this, you could try refluxing the reaction using a Dean-Stark apparatus to remove water from the reaction (water formation retards the condensation reaction). I found that adding a small amount of MgSO4 to the reaction promotes the condensation reaction as well (of course you need to use a non-alcohol solvent when using MgSO4).
Dear Ja M.
In general, the formation of imines (including alpha, beta-unsaturated imines) in apolar and aprotic solvent requires the presence of a catalyst that will help in the transfer of protons in the steps of carbinolamine formation and in its decomposition. In a recent study by our research group, it was verified that methanesulfonic acid has a superior performance than acetic acid, making it possible to use relatively low amounts of this catalyst (Rufino, V. C.; Pliego Jr, J. R. J. Braz. Chem. Soc. 2023. https://dx.doi.org/10.21577/0103-5053.20230063). Experimentally, molecular sieves are also used as additives (A. D. J. Calow, J. J. Carbo, J. Cid, E. Fernández, A. Whiting, J. Org. Chem. 2014, 79, 5163).
Some works of our research group in which the investigation of the reaction mechanisms of imine formation in aprotic solvent was conducted:
Rufino, V.C.; Pliego Jr., J.R.; Computer Theor. chem. 2020,
1191, 113053. https://doi.org/10.1016/j.comptc.2020.113053
Rufino, V.C., Pliego, J.R., J Phys Org Chem 2023, 36(3), e4467. https://doi.org/10.1002/poc.4467
Rufino, V.C.; Pliego Jr, J.R.J. Braz. chem. Soc. 2023. https://dx.doi.org/10.21577/0103-5053.20230063
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