Abstract
Fourteen kinds of N-(5-halofurfurylidene)-arylamine (B) (Table I) was prepared by the reaction of 5-halofurfural (halogen=Cl or Br) and aromatic primary amines in cold ether solution. (B) was also formed by the reaction of 5-halofurfural and N-benzylidenearylamine. Of the compounds (B) so formed, N-(5-halofurfurylidene)-anilines (I and X) reacted with aniline to produce N-(5-anilinofurfurylidene)-anilines (A), and with sodium ethoxide to form N-(5-ethoxyfurfurylidene)-aniline, (B) formed (A) on merely heating (B) with alcohols and this reaction mechanism was assumed to be as indicated by formulae (3), (4), and (1).
Application of benzylamines to (I) was found to effect exchange reaction of the amines. Reduction of (X) with sodium borohydride to N-(5-bromofurfuryl) aniline and its reaction with aniline ended in complete recovery of the starting compound.
