Patent GB-753976-A (GB)
Title: Novel amides, their production and use
IPC: C07C233/16
Filed: 1954-10-21
Abstract: The invention comprises amides of the general formula <FORM:0753976/IV(a)/1> in which Ar is a phenyl radical which may be substituted by alkyl, alkoxy, halogen and/or nitro groups, X is oxygen or sulphur, Alk is an alkylene radical, R1 is hydrogen, alkyl, alkenyl or aralkyl and R2 is an a :b -unsaturated aliphatic hydrocarbon radical, and their preparation by reacting an amine of the formula <FORM:0753976/IV(a)/2> or a reactive derivative thereof such as a salt or the corresponding carbamyl halide with an acid of the formula R2-COOH or a functional derivative thereof, by known methods for acylating an amine.  Alternatively the acid R2COOH in the above process may be replaced by a corresponding acid or functional derivative thereof in which the double bond has been replaced by atoms or groups which may be eliminated to form the required a :b -double bond, and the product is treated to eliminate these substituents.  The amides may also be prepared by treating a reactive ester of an alcohol of the formula <FORM:0753976/IV(a)/3> with a phenol or thiophenol ArOH or ArSH or a salt thereof, or by treating a reactive ester of an alcohol of the formula ArX-Alk-OH with an amide of the formula <FORM:0753976/IV(a)/4> or by treating a reactive ester of an alcohol of the formula R1OH with an amide of the formula <FORM:0753976/IV(a)/5> Numerous examples are given of products of the formula I in which "Ar" is chosen from phenyl, p-nitrophenyl, p-methoxyphenyl, o- and p-methylphenyl, 2:4- and 3:5-dimethylphenyl, 2:4:6-trimethylphenyl and o- and p-chlorophenyl radicals, X is oxygen, Alk is an ethylene or isopropylene chain, R1 is hydrogen or a methyl, ethyl, n-propyl, isopropyl, n-butyl or benzyl radical and R2 is a crotonyl or dimethacrylyl radical also there is prepared as a compound in which X is sulphur, b :b -dimethylacrylic acid N-b -(4-chlorophenyl mercapto) ethyl-amide.ALSO:Preparations having pharmaceutical, insecticidal, acaricidal and fungicidal properties comprise amides of the general formula <FORM:0753976/VI/1> (see Group IV(b)), in which Ar is a phenyl radical which may be substituted by alkyl, alkoxy, halogen and/or nitro groups, X is oxygen or sulphur, Alk is an alkylene radical and R2 is an b  : b -unsaturated aliphatic hydrocarbon radical, dispersed in a diluent or solvent which may suitably be a solid, a semi-solid, or a liquid.  Specified solid diluents include tricalcium phosphate, calcium carbonate, kaolin, bole, bentonite, talcum. magnesia usta, kieselguhr, boric acid, cork powder and sawdust, which may be made wettable by the addition of wetting or dispersing agents. Semi-solid vehicles include petroleum jelly and wool grease. Liquid preparations include solutions in solvents such as isopropanol or high boiling oils, e.g. vegetable oils; emulsions dispersed by means of emulsifiers such as soaps, sulphonated fats, fatty acid esters, fatty acid sulphonates, quaternary ammonium compounds and condensation products of ethylene oxide, and aerosols in which the active component is dispersed in a solvent which boils below room temperature such as difluorodichloromethane.  Examples are given of preparations in which the active component is crotonic acid-N-ethyl-N-b -phenoxy-ethylamide or b  : b  - dimethyl - acrylic acid - N - ethylN - b  - phenoxy - ethylamide.