Convenient synthesis of 1-alkyl-2,5-bis(thiophenylmethylene)pyrroles using the mannich reaction

Article abstract of DOI:10.1016/S0040-4039(97)10786-9

Aminomethylation of 1-alkylpyrrole (alkyl: hydrogen, methyl, hexyl, dodecyl) by aqueous formaldehyde and dimethylamine hydrochloride, followed by reaction with iodomethane, affords the 1-alkyl-2,5-bis[(trimethylamino) methyl]pyrrole diiodide. These diiodide salt derivatives react with sodium thiophenoxide to give 1-alkyl-2,5-bis(thiophenyl methylene) pyrrole yielding monomers found to be useful for synthesizing new conducting polymers.