[CONTRIBUTION
CHEMICAL LABORATORY OF
FROM THE
SWARTFIMORE
COLLEGE]
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
