From 13.1 g of N-p-chlorobenzyl-2-nitroaniline (MP 110°C, obtained in the
form of orange-red needles, from o-nitrochlorobenzene and pchlorobenzylamine by reaction for 3 hours at 150°C) by reduction with Raneynickel and hydrogen, in which reaction the substance may be suspended in
methanol or dissolved in methanol-ethyl acetate at normal pressure and at
about 40°C with combination of the theoretical quantity of hydrogen, 12.2 g
are obtained of o-amino-N-p-chlorobenzylaniline, which after recrystallization
from aqueous methanol has a MP of 90°C.
8 g of o-amino-N-p-chlorobenzylaniline and 2.8 g of pyridine are dissolved in
dry ether and reacted with an ethereal solution of 3.9 g of chloracetyl chloride
with cooling in a mixture of ice and common salt. 8 g of N-p-chlorobenzyl-N'-
chloracetyl-o-phenylene diamine are obtained which can be worked up in the
form of the crude product and, in the slightly colored form, has a MP of
130°C.
7.6 g of this compound are boiled with 3.9 g of pyrrolidine in 70 cc of toluene
for some hours under reflux. After extraction by shaking with water and
treatment with hydrochloric acid the hydrochloride is produced of N-pchlorobenzyl-N'-pyrrolidylacetyl-o-phenylene diamine together with some 1-pchlorobenzyl-2-N-pyrrolidylmethyl-benzimidazole. The former, after
recrystallization from butanol, melts with foaming at 205°C, the latter, after
recrystallization from butanol melts at 239°C to 241°C, and is in the form of
white microscopic rods. Boiling in nitrobenzene converts the former compound
into the latter.
