How would one go about separating a solid mixture of regioselectively alkylated solids. I'll give a specific example.

Take the hypothetical alkylation of methylpentazole with MeI.

There are three (3) different products possible. How would you go about the separation of these products after recrystallization of the product mixture (with the assumption the reactants and products don't explode).

The problem is that you cannot simply distill off each part of the mixture due to the high boiling point of the solids.

  • $\begingroup$ Do they show separation by HPLC? $\endgroup$
    – Waylander
    Commented Jul 28, 2017 at 12:34
  • $\begingroup$ This is hypothetical, but I would assume that two of the products would not separate, namely the 2- and 3- methylated salts. And the third salt would probably not form anyways due to loss of aromaticity. $\endgroup$
    – AS_1000
    Commented Jul 28, 2017 at 20:36
  • $\begingroup$ Then I think it would be a real struggle to separate the isomers $\endgroup$
    – Waylander
    Commented Jul 29, 2017 at 11:14


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