Patent GB-810539-A (GB)
Title: Process for the production of new aryloxy acetic acid amides
IPC: C07D295/185
Filed: 1957-10-31
Abstract: The invention comprises compounds of the general formula <FORM:0810539/IV (b)/1> where R1 is alkyl, alkenyl, cycloalkyl or a phenyl or benzyl radical which may be substituted by halogen or C1-C6 alkyl or alkoxy groups.  R2 is hydrogen or C1-C4 alkyl or alkenyl radical, or R1 and R2 represent alkylene groups bound to each other direct or by way of an oxygen atom, R3 is alkyl, R4 C1-C6 alkyl, and R5 hydrogen or C1-C3 alkyl.  The compounds may be prepared by reacting an aryloxy acetic acid or reactive functional derivative thereof, with a primary or secondary amine.  Suitable functional derivatives are the halides, mixed anhydrides with aliphatic carboxylic acids, e.g. acetic acid and esters thereof, preferably C1-C5 alkyl esters and the phenyl ester.  The reactions are preferably carried out in the presence of a solvent, e.g. ether, benzene hydrocarbons, water or alcohols.  Other substances which may be present in the reaction medium depending upon the reactants are e.g. excess amine, pyridine, dimethyl aniline, or sodium or potassium carbonate.  Suitable aryloxy acetic acids specified are 2-methoxy 4-substituted phenoxy acetic acids, where the 4 substituent is methyl, ethyl, propyl, n-butyl, n-amyl, isoamyl, n-hexyl, n-heptyl, n-octyl; 2-ethoxy 4-substituted phenoxy acetic acids where the 4-substituent is ethyl, n-propyl, n-butyl; 2-methoxy 5-substituted phenoxy acetic acids where the 5-substituent is ethyl, n-propyl, n-butyl, n-amyl; 2 - ethoxy - 5 - n - propyl phenoxy acetic acid, 2-methoxy 6-substituted phenoxy acetic acids in which the 6-substituent is methyl, ethyl, n-propyl, n-butyl, n-amyl; 2-ethoxy 6-n propyl phenoxy acetic acid, 2-methoxy, 3-methylphenoxy acetic acid, a -(2-methoxy-4-n-propylphenoxy) propionic acid and a -(2-methoxy-4-n-propylphenoxy) butyric acid.  Among suitable amines specified are methyl, ethyl, n-propyl, sec. butyl, isoamyl, n-hexyl, allyl, methallyl, cyclopentyl, cyclohexyl, cyclohexylmethyl, benzyl, b  - phenyl - ethyl, dimethyl, methyl - ethyl, diethyl, dimethallyl, methyl n-propyl, di-n-butyl, di - n - propyl, methyl - n - butyl, methyl-allyl, diallyl N-methyl cyclohexyl and N-methyl benzylamines, toluidines, pyrrolidine, piperidine and N-alkyl or N-alkenylarylamines such as N-methyl, N-ethyl, N-n-propyl, N-methallyl, N-allyl or N-crotyl-, mesidine, bromaniline 3,5-dichloraniline and p-phenetidine.  A further method for the preparation of the compounds of the invention is by reacting a carbaminyl chloride of general formula <FORM:0810539/IV (b)/2> where R1 has the meaning given above and R12 has the meaning given above for R2 but excluding hydrogen, in the warm with the salt of an aryloxy acetic acid, in particular an alkali salt.  Suitable carbaminyl chlorides are those derived from the specified amines. The compounds of the invention may also be prepared by reacting a halogen acetamide of general formula <FORM:0810539/IV (b)/3> with an alkoxy alkyl phenol, in the presence of an acid binding agent, or with the salt of such a phenol, e.g. an alkali metal salt.  The compounds of the invention may also be prepared by reacting a compound of the above general formula, in which R3 is an alkenyl radical instead of alkyl with catalytically activated hydrogen until one mol. has been taken up.  Many examples are given.  Specification 792,490 is referred to.