Patent GB-805505-A (GB)
Title: Substituted benzoylacetanilides
Inventor: CORBY NEVILLE SLATER
IPC: G03C7/36
Filed: 1956-05-22
Abstract: The invention comprises compounds of the general formula <FORM:0805505/IV (b)/1> where R1 and R2 are alkyl, aralkyl, aryl or cycloalkyl, which can be the same or different or R1 and R2 are joined together to form with the nitrogen atom a heterocyclic ring, Y is an aryl radical and X is a hydrogen or chlorine atom.  The radicals represented by R1 and R2 may be substituted with chlorine, bromine, methyl, ethyl, butyl, dodecyl, octadecyl, methoxy, ethoxy or similar groups.  Y may be substituted by amino, N-methyl-N-octadecylamino, carboxylic, sulphonic, nitro, methyl, methoxy, trifluoromethyl, chlorine, acetylamino or other similar groups.  Those compounds in which Y is not substituted with an amino group are prepared by heating an aromatic amine of formula YNH2 with an ester of formula <FORM:0805505/IV (b)/2> where R3 is an alkyl radical, e.g. methyl or ethyl, and subsequently replacing a hydrogen atom of the CH2 group, by chlorine, by treatment with phosphorus pentachloride if desired. The process may be carried out by heating the reagents together in an inert solvent, e.g. xylene, chlorobenzene, pyridine, and the product isolated by distilling off some or all of the solvent, cooling and filtering.  The esters used as starting materials may be made by condensing the appropriate p-disubstituted aminobenzoyl chloride with alkyl acetoacetate and sodium alkoxide or with the sodium alkyl acetoacetate, and hydrolysing the p-disubstituted aminobenzoylacetoacetic ester so formed.  The p-disubstituted aminobenzoyl chloride may be made from the appropriate N : N-disubstituted aniline by treating it with phosgene, hydrolysing with caustic soda, separating the carboxylic acid and treating it with thionyl chloride.  Suitable esters are methyl or ethyl-p-dimethylaminobenzoylacetate; ethyl p-N-ethyl - N - benzyl - aminobenzoylacetate, ethyl-p - piperidino - benzoylacetate, ethyl - p - N-ethyl - N - cyclohexylbenzoylacetate, and ethyl - p - N - methyl - N - phenylaminobenzoylacetate.  Suitable amines are 3-amino-4-N-methyl - N - octadecylamino benzoic acid, sulphanilic acid, 3 - amino - 4 - N - methyl - N-octadecyl - amino - benzene sulphonic acid, 5 - diethylsulphamyl - 2 - methoxy - aniline, 3 - amino - 4 - chloro - benzotrifluoride, 2 : 5-dimethoxyaniline, 4 - amino - 41 - chloro - diphenyl ether, o - toluidine, p - nitroaniline, o - amino - N : N - dimethylaniline or aniline. Those compounds of the invention, in which Y is substituted with an amino group are prepared by reduction of the corresponding nitro compound, by treating a solution of the nitro compound in, e.g. water or acetic acid, with a reducing agent such as iron, filtering the resulting amino compound, or distilling off some or all of the solvent and then cooling and filtering.  Those compounds in which Y is substituted with an acylamino group may be prepared by acylating the corresponding unsubstituted compound with an acylating agent such as octadecenylsuccinic anhydride. Examples are given of the preparation of p-dimethylamino - benzoylacet - (2 - N - methyl - N - octadecylamino - 5 - carboxy) anilide; p - N - benzyl - N - ethylaminobenzoylacet - (2 - N - methyl - N - octadecylamino - 5 - carboxy) anilide; p - dimethylaminobenzoylacet (2 - N - methyl - N - hexadecyl - amino - 5 - carboxy) anilide; p - dimethylaminobenzoylacet - (2 - dimethylamino - 5 - carboxy) anilide; p - dimethylaminobenzoylacet - (5 - diethylsulphamyl - 2 - methoxy) anilide; p - dimethylaminobenzoylacet - (2 - chloro - 5 - trifluoromethyl) anilide; p - dimethylaminobenzoylacet - (2:5 - dimethoxy) anilide; p - dimethylaminobenzoylacet - (41 - [411 - chlorophenoxyl] - ) anilide, p - dimethylaminobenzoylacet - o - toluide; p - dimethylaminobenzoylacetanilide-4 - sulphonic acid; p - dimethylaminobenzoylacet - 4 - nitro - anilide; p - dimethylaminobenzoylacet - 4 - amino - anilide; p - piperidinobenzoylacet - (2 - N - methyl - N - octadecylamino - 5 - carboxy) anilide; p - N - methyl - N - phenylaminobenzoylacet - (2 - N - methyl-N - octadecylamino - 5 - carboxy) anilide; p - N - benzyl - N - ethylaminobenzoyl - alpha-chlor - acet - (2 - N - methyl - N - octadecylamino - 5 - carboxy) anilide; and p - N - dimethylaminobenzoylacet - 4 - (alpha - carboxymethylene - alpha - octadecenyl - acetamido)-anilide.