2-Aminothiophenol → HCID 19421152, compound

Participants

Reaction Steps

Scheme XII below shows the synthesis of two monomers containing electron withdrawing heterocyclic groups. In the presence of triethylamine, 1-(4-bromobenzoyl)-2-benzoylhydrazine and p-bromophenylacetic acid is converted to the corresponding acid chloride followed by reaction with benzoic hydrazide that cyclizes in the presence of phosphorus chloride to give 2-(4-bromophenyl)-5-phenyl-1,3,4-oxadiazole. The bromine group reacts with NaCN to form a cyano group that is then reduced by diiodobutylaluminum hydride to obtain an aldehyde group. This is finally converted to dichloromethyl groups with PCl5. p-Bromophenylacetic acid reacts with 2-aminothiophenol in polyphosphoric acid to give 1-(benzothiazol-2-yl)-methyl-4-bromobenzene. This is then converted to the 1-(benzothiazol-2-yl)-methyl-4-dichloromethyl benzene in three steps, as indicated. ##STR10##

Provenance & Evidence