>>13135466Ok,
>>13139246 here with a more elaborate post.
Lets do some reaction troubleshooting.
Step 1:
Confirm that all your starting material is consumed. Do this by TLC/NMR/quant. MS
(TLC would obviously be the quickest). You mentioned that only the product does not dissolve, but your starting material definitely should, so with TLC you should be able to check if there is still starting material left in your reaction.
Full conversion? -> Move on to step 2
No full (or significant) conversion? -> Try a different method; eg. longer reaction time, higher T, different solvent, etc.
Step 2:
Check your crude product (the crud in your flask after solvent evaporation) by NMR/quant. MS. You want to see what your SM is actually reacting to. You mentioned solubility issues, have you tried DMSO? It's notorious for dissolving pretty much anything. Also, in the literature, NMR spectra of your compound are taken in chloroform. So it should also dissolve in that.
(Near) full conversion to your desired product -> Move on to step 3
(Significant) conversion into side products -> change method, do some lit. research.
Step 3: make sure you aren't losing significant amounts of products during washing (extremely unlikely, based on your previous solubility issues, but might be good to know for sure). Just TLC each of your wash fractions after washing your product.
That's everything I could think of this quick. This method is generally used to prepare your compound in the literature, so it should work. I'll be posting a slightly different experimental I found, might also be useful.
