Manufacturing Process
62 grams of para-tertiany-butyl-ortho,ortho'-dimethyl-phenyl-acetonitrile
[obtainable, for example, by the method of Buu-Hoi and P. Cagniant, Bulletin
de la Societe Chimique de France, volume 9, page 891 (1942)], 20.6 grams of
ethylenediamine of 96% purity and 1.55 cc of carbon disulfide are heated
together in a distillation flask with the exclusion of moisture for 48 hours on a
boiling water bath. Ammonia is evolved. Upon cooling the reaction product
solidifies and is then dissolved in benzene, the solution is filtered while hot
with the addition of animal charcoal and petroleum ether is added. The
mixture is filtered to remove the impurities that are first precipitated and by
the further addition of petroleum ether 2-(para-tertiary-butyl-ortho,ortho'-
dimethyl-phenyl-methyl)-imidazoline is caused to crystallize out.
The product melts at 131° to 133°C after being recrystallized from a mixture of benzene and petroleum ether. It can be converted into its hydrochloride as
follows:
189 grams of 2-(para-tertiary-butyl-ortho,ortho'-dimethyl-phenyl-methyl)-
imidazoline are dissolved in 400 cc of absolute ethanol, the solution is
rendered acid by the addition of 104 cc of an ethanolic solution of hydrochloric
acid of 30% strength, the mixture is filtered with the addition of animal
charcoal, and dry ethyl acetate and absolute ether are added until
crystallization sets in. After cooling the mixture, the salt is filtered off with
suction and crystallized several times from absolute ethanol with the use of
animal charcoal and the addition of dry mixture of ethyl acetate and ether.
The hydrochloride so obtained melts at 327° to 329°C (with decomposition).
Safety Profile
Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx and HCl.
