Patent GB-1016826-A (GB)
Title: Acylamino compounds and a process for preparing them
Inventor: MERTEN RUDOLF
IPC: C07D211/70
Filed: 1963-01-10
Abstract: The invention comprises acylamino compounds of the general formulae <FORM:1016826/C2/1> iu which R is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, aryl, or methoxymethyl; R1 is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, or aryl radical; R11 is a methyl, dihalomethyl, isopropenyl, cycloalkyl, aryl, alkoxy, aryloxy, alkylamino or arylamino radical; Y is a haloethyl, alkoxyethyl, a carboxylic acyloxyethyl, alkoxyalkenyl or alkenyl group containing 2 to 4 carbon atoms, said ethyl and alkenyl groups being substituted by alkyl and/or aryl radicals; Z is an -O- or -NH- radical; and R2 is a hydrogen atom, an alkyl radical of 1 to 4 carbons, a cycloalkyl or aryl radical. These compounds may be made by reacting a derivative of an acylated amine, of the formula <FORM:1016826/C2/2> in which X is a halogen atom, an acyloxy, alkoxy or aryloxy radical and R, R1 and R11 have the meanings above, with a compound which contains a > C = C < double bond, or a product which reacts as a conjugated diene in a diene synthesis, and separating the product formed from the reaction mixture.  The starting material may be an olefine of the general formula <FORM:1016826/C2/3> wherein R12 is a hydrogen atom, an alky radical having 1 to 4 carbon atoms, an alkenyl radical of 1 to 4 carbon atoms, a cycloalkyl radical, an aryl radical or a vinylaryl radical or two radicals together form a cycloaliphatic ring.  The reaction may be effected without a catalyst or in the presence of a Lewis-acid or an organic sulphonic acid in an amount up to 20 mol. per cent of the acylated amine derivative, said reaction being carried out under anhydrous conditions in a non-polar solvent at a temperature of from -40 DEG  to 180 DEG  C.  Methods for making the acylated amine starting materials are outlined.  Alkoxymethyl carbamic acid esters may be made from alkoxy acetamides with bromine and alkali metal alcoholates, or from alkoxy acetic acid azide with absolute alcohol.  The hydroxymethyl derivatives are obtained from aqueous formaldehyde solution and carbamic acid esters.  Examples are given of the preparation of N-alkyl-N-chloromethyl carbamic esters from 1,3,3-trimethyl-hexahydro-s-triazine and chloroformic esters; alkoxymethyl carbamic esters from N-alkyl-N-chloromethylcarbamic acid chlorides and sodium alcoholates; or from carbamic acid ethyl ester, formaldehyde and an alcohol; N-chloromethyl-N-acyl-amines are made from 1,3,5-trimethylhexahydro-s-triazine and an acid chloride. N - alkyl - N - acyloxymethyl carboxylic acid amides are made from the above triazines and carboxylic acid anhydrides. N-alkyl-N-a -acyloxyalkyl carbamic esters or carbonamides are made from N-alkyl-N-haloalkyl carbamic esters or carbonamides and alkali metal salts of carboxylic acids.  Detailed examples of the preparation of the novel acylamino compounds are given.ALSO:Herbicidal action is shown in aqueous emulsion by acylamino compounds of the general formulae <FORM:1016826/A5-A6/1> in which R is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, aryl or methoxymethyl, R1 is a hydrogen atom or an alkyl, alkenyl, cycloalkyl or aryl radical; R11 is a methyl, dihalomethyl, isopropenyl, cycloalkyl, aryl, alkoxy, aryloxy, alkylamino or arylamino radical; Y is a haloethyl, alkoxyethyl, a carboxylic acyloxyethyl, alkoxyalkenyl or alkenyl group containing 2 to 4 carbon atoms, said ethyl and alkenyl groups being substituted by alkyl and/or aryl radicals; Z is an -O- or -NH- radical; and R2 is a hydrogen atom, an alkyl radical of 1 to 4 carbons, a cycloalkyl or aryl radical.