Patent GB-736630-A (GB)
Title: N-aryl-n-aminoalkyl ureas and method of producing the same
IPC: C07C275/28
Filed: 1953-06-05
Abstract: The invention comprises N-aryl-N1-aminoalkyl ureas corresponding to the formula <FORM:0736630/IV (b)/1> wherein R1 represents hydrogen or the methyl group, R2 represents hydrogen or an alkyl group having from 1 to 3 carbon atoms, "alkylene" represents an alkylene radical with 2 or 3 carbon atoms and Am represents a dialkylamino group, the alkyl groups of which each have from 1 to 4 carbon atoms, an alkylene imino group with 5 or 6 ring members or the morpholino group. Such compounds are obtained by reacting a reactive functional derivative of 2.6-dimethyl- or 2.4.6-trimethyl-carbanilic acid (e.g. the isocyanate or urethane) with a diaminoalkane of the formula R2HN-alkylene-Am.  As an alternative a secondary amine of the formula Am-H is reacted with an N-aryl-N1-halogenalkyl urea of the formula <FORM:0736630/IV (b)/2> or with an N-aryl-N1-ethylene urea of the general formula  <FORM:0736630/IV (b)/3> The N-aryl-N1-halogenoalkyl ureas can be prepared by reacting 2.6-dimethyl- or 2.4.6-trimethylphenylisocyanate with chloralkyl- or bromalkylamines. As diaminoalkanes for use in the first process are specified N-(b -aminoethyl) -, N - (b  - amino - propyl) -, N - (b -aminoisopropyl) -, N - (g  - amino - propyl, N-(b  - methylaminoethyl) -, N - (b  - ethylaminoethyl) -, N - (b  - methylaminopropyl) -, N - (b -methylamino - isopropyl) -, and N - (g  - methylamino - propyl) - dimethylamine, - methylethylamine, - diethylamine, - dipropylamine, - dibutylamine, - pyrrolidine, - 2 - methylpiperidine and -morpholine. The products can be converted into salts with, for example, hydrochloric, hydrobromic, sulphuric, phosphoric, methane sulphonic, ethane disulphonic, malic, succinic, tartaric, benzoic and phthalic acids.  In examples (1) 2.4.6-trimethyl-phenylisocyanate (obtained by reacting mesidine hydrochloride with phosgene) is reacted with N.N-diethyl - N1 - methyl - ethylene diamine to give N - (2.4.6 - trimethyl - phenyl) - N1 - methyl - N1-(b  - diethylamino - ethyl) - urea; (2) N - (2.4.6-trimethylphenyl) - N1 - ethyl - N1 - (b  - dimethylamino - ethyl) - urea is prepared similarly.  A list is given of analogously prepared compounds containing various N1-ethyl, propyl or isopropyl groups and N1-dimethylaminoethyl and propyl groups, an N1-diethylaminoethyl group or a b -pyrrolidinoethyl group; (3) 2.6-dimethyl-phenylisocyanate (from the reaction of phosgene with 2.6-xylidine hydrochloride) is reacted with N.N - dimethyl - N1 - isopropyl - ethylene diamine to give N - (2.6 - dimethyl - phenyl)-N1 - isopropyl - N1 - (b  - dimethylamino - ethyl)-urea.  A list is given of similar compounds with other N1-alkyl substituents and also with N1-piperidinoethyl- and g -morpholino-propyl substituents; (4) 2.6-dimethyl-phenyl urethane (from 2.6-xylidine and ethyl chloroformate) is reacted with N.N-diethylethylene diamine to give N - (2.6 - dimethylphenyl) - N1 - (b  - diethylaminoethyl) - urea; (5) N - 2.6 - dimethylphenyl) - N1 - (b  - brom - ethyl) - urea (from 2.6-dimethylphenylisocyanate and b -bromethylamine) is reacted with diethylamine to give the same product as in example (4).