Patent GB-726080-A (GB)
Title: New halogen-containing amino fatty acid anilides, their addition salts and their production
IPC: C07C233/02
Filed: 1953-02-09
Abstract: The invention comprises anilides of the general formula <FORM:0726080/IV (b)/1> where halogeno represents chlorine or bromine, R represents hydrogen or an alkyl radical containing not more than 4 carbon atoms, Acyl represents the radical of a straight or branched chain fatty acid containing not more than 6 carbon atoms and X represents the radical of a primary or secondary amine attached to the alkyl chain of the fatty acid, and acid addition salts of said anilides, and a process for the preparation of the anilides by reacting a halogeno methyl aniline of the general formula <FORM:0726080/IV (b)/2> wherein R and halogeno have the above significance, or a salt thereof, with a reactive derivative of a halogeno fatty acid containing not more than 6 carbon atoms to form the corresponding halogen fatty acid 2-halogeno-6-methylanilide, and further reacting the latter compound with a primary or secondary amine. Other methods which may be used to prepare the above anilides are reacting a halogeno methyl aniline of the above general formula, or a salt thereof, with a reactive derivative of the required amino fatty acid, reacting anilides of the above general formula where R represents hydrogen with an alkylating or aralkylating agent, or the corresponding unsaturated fatty acid halogeno-methyl anilides, e.g. the corresponding amide of acrylic acid, are reacted with secondary amines to form b -N,N-dialkylamino fatty acid 2-halogeno-6-methyl anilides.  Compounds yielding the fatty acid radical -Acyl-X of the above general formula include reactive derivatives of dialkylamino acetic acids, lower alkyl esters of N,N-dibenzylamino acetic acid, and reactive halogeno fatty acid derivatives such as chloracetic acid anhydride, chloracetyl chloride, a - and b - chlorpropionic acid chloride, a - and b -bromopropionic acid bromide, and a -bromobutyric acid bromide.  The radical X may be derived from n-butylamine, allylamine, dimethyl- and diethyl - amine, morpholine, piperidine, a - methylpiperidine, pyrrolidine, cyclohexylamine and benzylmethylamine.  When the anilides are prepared by the alkylating reaction referred to above, it is preferred to use the anilide in the form of an N-alkali metal salt, and the alkylating agent may be an ester of an alkanol with a strong inorganic acid, e.g. with a hydrohalide, sulphuric acid or an alkyl- or aryl-sulphonic acid ester of an alkanol.  The salts of the anilides may be prepared from inorganic or organic acids, e.g. from hydrochloric, tartaric and citric acids.  In the examples the following compounds are prepared:-diethylamino-, dimethylamino-, N-morpholino-, N-piperidino-, N-pyrollidino-, N-b -methylpiperidino and n-butylamino - acetic acid 2 - chloro - 6 - methylanilides and their hydrochloride salts, b -N,N-diethylamino-isobutyric acid 2-chloro-6-methylanilide, g  - N,N - diethylamino - propionic acid 2 - chloro - 6 - methylanilide, g  - N,N - dimethylamino-propionic acid 2-chlor-6-methylanilide and its hydrochloride salt, N-pyrollidino-acetic acid N1-methyl-2-chloro-6-methylanilide and its hydrochloride salt and N,N-diethylamino-acetic acid N1-methyl-2-chloro-6-methylanilide and its hydrochloride salt.  A number of additional compounds are referred to including 2-bromo-6-methylanilides of the above general formula.  Amino-acetic acid 2-chloro-6-methylanilide is obtained in the form of its hydrochloride salt by heating chloracetic acid 2-chloro-6-methylanilide with ammonia in an autoclave and treating the reaction product with sodium chloride.  Methacrylic acid 2-chloro-6-methylanilide is obtained by reacting 2-chloro-6-methylaniline and methacrylic acid chloride.  Chloracetic acid 2-chloro-6-methylanilide is prepared by reacting 2-chloro-6-methylaniline and chloracetyl chloride.