102

Unprimei Roman numerals in the text mean R = CHs; w-3n primed, R = C~HE.. The present investigation consists of a more careful study of the action of ...
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ETHYLENEDIAMINE. V.' THE ACTION OF AROMATIC ACID CHLORIDES ON 4,5-DIHYDROIMIDAZOLES I N AQUEOUS MEDIA SAMUEL R. ASPINALL Received August 4, iQdi

It is known that imidazoles and benzimidazoles of simple structure, although possessing a nitrogenous ring which in general is very stable, readily undergo ring fission when subjected to a Schotten-Baumann reaction even a t 0". CH-N

1

CHi\;HCOC6H6

CsHsCOCl -j

/cH

aq'NaoH

I1

+ HCOOH

CHNHCOC6Hs

CH-NH

This remarkable vulnerability of a very stable ring has been the subject of m,my investigations. Gerngross (1) allowed benzoyl chloride to act on benzimidazole under a variety of conditions, and obtained several compounds which he showed to be intermediates and postulated the mechanism shown in formulas A-E.

+

CeH&OCI aq. KaOH

+

@::CH

-

COCeHs 0-N; -N

CH

COC&

/./N C'i

K - l C H

\

"COCeHs

COCsHs --+@C