Dear all,

I'm working in a coupling reaction with CDI (Carbonyldiimidazole), where the first reaction is the activation of the Acid with CDI.

The product is an easily hydrolizable Imidazolide, but it doesn't react that quickly with Methanol, for example.

Has anyone worked in determining imidazolide content in a reaction mixture by HPLC?
When I try to make this determination with AcN/Water mobile phases, I just see the acid (as expected).

The fact is that derivitizing the sample with methanol is not an option for now, since it's slow and I'm not sure about the completion of this reaction.

Has anyone some experience derivitizing imidazolides with Dimethylamine? Aqueous methylamine? Diethanolamine?
Any other amine or molecule?

Thanks in advance!

Extra info: when running the sample in a Sílica TLC plate, I see 3 spots when I spot the plate 5-10 minutes and heating after quenching with methanol which would account for the Acid + Imidazolide + Methyl-esther.
When I repeat the same TLC a day later, I only see the Methyl-esther spot.