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1-[2,4-Dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]-3-(p-methylbenzyl)imidazolium bromide; mp. 152.2° C., by the reaction of 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]-imidazole and p-methylbenzyl bromide.
1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-[N-(2,5-dimethoxyphenyl)carbamoylmethyl]imidazolium chloride monohydrate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In acetonitrile;
EXAMPLE XXXIII In a similar operation and employing recovery techniques similar to Example XXXII, but employing different amounts of reactants or different purification techniques as indicated, the following compounds are prepared: 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]-3-[N-(2,5-dimethoxyphenyl)carbamoylmethyl]imidazolium chloride monohydrate, m.p. 121.1° C., by (a) refluxing for 2 days, 4.2 parts of 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazole, 2.5 parts of 2-chloroaceto-2',5'-dimethoxyanilide and 40 parts of acetonitrile, (b) recovering as in Example XXXII, and (c) washing the crude product with ether.
EXAMPLE XVI 15 parts of 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)-phenethyl]imidazole and 60 parts of 2,4-dichlorobenzyl chloride are mixed together in 120 parts of acetone as solvent and the resulting mixture is stirred at reflux temperature for 40 hours. At the end of this period, the mixture is warmed to evaporate off most of the solvent and the residue is poured onto diisopropyl ether, whereupon the 1-(2,4-dichlorobenzyl)-3-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazolium chloride product separates as an oil. The ether is decanted off and the oily residue is washed with warm xylene and thereafter triturated in 2-propanol whereupon the oily product solidified. The solid product is filtered off, washed with 2-propanol and dried to obtain a purified product, 1-(2,4-dichlorobenzyl)-3-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]-imidazolium chloride, mp. 178.9° C.
1-[2,4-Dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]-3-(m-methylbenzyl)imidazolium bromide; mp. 99°-101° C., by the reaction of 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]-imidazole and m-methylbenzyl bromide.
1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]3-n-octylimidazolium bromide; mp. 141.5°-143° C., from 1-[2,4dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazole and n-octyl bromide after an overnight reflux.
1-decyl-3-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazolium bromide; mp. 90°-94° C., by the reaction of 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazole and n-decyl bromide after an overnight reflux.
1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-[N-(2,6-xylyl)carbamoylmethyl]-imidazolium chloride hydrate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]-3-[N-(2,6-xylyl)carbamoylmethyl]-imidazolium chloride hydrate, m.p. 143°-150° C., by the reaction of 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazole and 2-chloroaceto-2',6'-xylidide.
1-(2,4-dichlorocinnamyl)-3-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-imidazolium chloride[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In di-isopropyl ether; acetonitrile;
A. A mixture of 4.2 parts of 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazole, 2.7 parts of 2,4-dichlorocinnamylchloride and 40 parts of acetonitrile is stirred and refluxed overnight. Upon the addition of diisopropyl ether, the product crystallizes. It is filtered off and dried, yielding 5.8 parts of 1-(2,4-dichlorocinnamyl)-3-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]-imidazolium chloride; mp. 142.2° C.
EXAMPLE XV In a manner similar to that described in Examples XIII and XIV, 1-(p-bromobenzoylmethyl)-3-[2,4-dichloro-beta-(2,4 -dichlorobenzyloxy)phenethyl]imidazolium chloride is prepared by the reaction of 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazole and 4'-bromo-2-chloroacetophenone. The product after successive treatment steps of stirring with 4-methyl-2-pentanone, stirring a chloroform solution thereof with silica gel and triturating with 4-methyl-2-pentanone has a melting point of 198.2° C.