Patent GB-747592-A (GB)
Title: N-(substituted-benzyl)-n-(hydroxyalkyl or lower alkyl) dihaloacetamides and the preparation thereof
Filed: 1953-12-23
Abstract: The invention comprises N-substituted dihaloacetamides of the formula Ar-CH2-NR-CO-CH(Hal)2 where Ar is substituted phenyl, the substituents being one or more halogen, alkyl, alkoxy, methylenedioxy, ethylenedioxy, alkylthio, alkylsulphonyl or nitro groups, and R is alkyl, b -hydroxyalkyl or g -hydroxyalkyl having not more than 6 carbon atoms.  The products are made by acylating the appropriate substituted benzylamines with dihaloacetyl halides or (when R is hydroxyalkyl) alkyl dihaloacetates.  All the halogen atoms mentioned above can be chlorine, bromine, fluorine or iodine. Examples are given of the preparation of the following substituted dichloracetamides: N - (3:4 - dichlorobenzyl) - N - (2 - hydroxyethyl), N - (2:4-dichlorobenzyl) - N - (2 - hydroxyethyl), N - (p - chlorobenzyl) - N - (2 - hydroxyethyl), N - (p - ethoxybenzyl) - N - (2 - hydroxyethyl), N - (p - isopropylbenzyl) - N - (2 - hydroxyethyl), N - piperonyl - N - (2 - hydroxyethyl), N - (p - nitrobenzyl) - N - (2 - hydroxyethyl), N - (p - butoxybenzyl) - N - (2 - hydroxyethyl), N - (2:4 - dichlorobenzyl) - N - (2 - hydroxypropyl), N - (3:4 - dichlorobenzyl - N - (2 - hydroxypropyl), N - (o - chlorobenzyl) - N - (2 - hydroxyethyl), N - (3:4 - dichlorobenzyl) - N - (3 - hydroxy - propyl), N - (2:4 - dichlorobenzyl) - N - (3 - hydroxypropyl), N - (3:4 - dimethoxybenzyl) - N - (2 - hydroxyethyl), N - (2:4 - dichlorobenzyl) - N - isopropyl, N - (p - butoxybenzyl) - N - isopropyl, N - (p - isopropylbenzyl) - N - isopropyl, N - (p - nitrobenzyl) - N - isopropyl, N - (2:3 - dimethoxybenzyl) - N - ethyl, N - (2:4 - dichlorobenzyl) - N - n - butyl, N - (2:4 - dichlorobenzyl) - N - sec. - butyl, N - (3:4 - dichlorobenzyl) - N - n - butyl, N - (2:4 - dichlorobenzyl) - N - n - propyl, N - (3:4 - dichlorobenzyl) - N - isobutyl, N - (o - methoxybenzyl) - N - ethyl, N - (3:4 - dichlorobenzyl) - N - isopropyl, N - (p - chlorobenzyl) - N - isopropyl, N - piperonyl - N - isopropyl, N - (p - methylbenzyl) - N - isopropyl and N - (o - chlorobenzyl) - N - isopropyl.  The preparation of N - (2:4 - dichlorobenzyl) - and N - (3:4 - dichlorobenzyl) - N - (2 - hydroxyethyl) - dibromacetamides is also described.  Other products mentioned are N-(3:4:5-triethoxybenzyl) - N - (2 - hydroxypropyl) - dibromacetamide, N - (p - nitrobenzyl) - N - (2 - hydroxyethyl) - difluoracetamide, N - (3:4:5 - tribromobenzyl) - N - isopropyl - dichloracetamide, N - (3:4 - diethoxybenzyl) - N - isobutyl - dibromacetamide, N - (p - nitrobenzyl) - N - n hexyl - di - iodoacetamide, N - (2:4 - dichlorobenzyl) - N - isopropylbromochloracetamide, N - (p - n - butylthiobenzyl) - N - (2 - hydroxyethyl) - dichloroacetamide, N - (p - n - butylthiobenzyl) - N - isopropyl - dichloracetamide, N-(p-isobutylsulphonylbenzyl)-N-(2-hydroxyethyl) - dichloracetamide and N - (p - n - butylsulphonylbenzyl) - N - isopropyl - dichloracetamide.  Various other alkyl, alkoxy, alkylthio and alkylsulphonyl groups are mentioned as substituents in Ar and various alkyl and hydroxyalkyl groups for R.  Substituted benzylamines Ar-CH2-NH-R are made by reacting R-NH2 with a nuclearsubstituted benzyl halide or by catalytically reducing the reaction product of R-NH2 with a substituted benzylamine (probably a Schiff's base). Examples are given of the production of 2 - (p - isopropylbenzylamino) - ethanol, 2 - (p - methoxybenzylamino) - ethanol, 2 - (2:4-dichlorobenzylamino) - ethanol, N - isopropyl - 2:4 - dichlorobenzylamine and N - isopropyl - 4 - n - butoxybenzylamine. Other products are mentioned in which R is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec.butyl, 2-hydroxyethyl and 2-hydroxypropyl, and the nuclear substituents are methyl, isopropyl, methoxy, dimethoxy, ethoxy, methylenedioxy, butoxy, chloro, dichloro, tribromo, tri-iodo and nitro.