Patent GB-803119-A (GB)
Title: Improvements in or relating to salts of substituted 2-imidazolines
IPC: C07D233/18
Filed: 1955-02-23
Abstract: The invention comprises salts of substituted 2-imidazolines of the general formula: <FORM:0803119/IV (b)/1> wherein R represents a hydrocarbon radical of at least 4 carbon atoms, R2 represents (a) an aliphatic hydrocarbon radical containing 1 to 4 carbon atoms, (b) an hydroxy substituted aliphatic hydrocarbon group of 1 to 4 carbon atoms, (c) said (a) group having a single ether linkage therein, (d) said (b) group having a single ether linkage therein, (e) said (a) group having a single keto linkage therein, or (f) said (b) group having a single keto linkage therein; R3 represents (g) hydrogen, (h) an aliphatic hydrocarbon radical of 1 to 8 carbon atoms, (i) an hydroxy substituted aliphatic hydrocarbon radical of 1 to 8 carbon atoms, (j) said (h) group having one or more ether linkages therein, or (k) said (i) group having one or more ether linkages therein; R4 is (l) an aliphatic, aromatic or aromatic-aliphatic hydrocarbon radical of 1 to 12 carbon atoms, (m) an hydroxy substituted aliphatic, aromatic or aromatic-aliphatic hydrocarbon radical of 1 to 12 carbon atoms, (n) said (l) group having one or more ether linkages therein, (o) said (l) group having a CONH linkage therein, or (p) said (m) group having a CONH linkage therein; X represents SO3 or O-SO3; and M represents an alkali metal, e.g. sodium or potassium, and the preparation thereof by reacting together under pH conditions of approximately 7 to approximately 9, e.g. at a temperature of from 100 DEG  to 200 DEG  F., compounds of the following formulae: <FORM:0803119/IV (b)/2> and <FORM:0803119/IV (b)/3> wherein R1, R2, R3, R4, X and M have the above significance.  The group R2 may be any of the following groups: -CH2-, -C2H4-, -C3H4-, -C6H8-, -CH2-CHOH-CH2-, -CH2-CHOH-CHOH-CH2-, -C2H4O C2H4-, -CH2-CHOH-O-C2N4-, -CH2 -CO-CH2- and -CH2-CO-CHOH-.  It is preferable to add to a solution of compounds of the general formulae I and II above, e.g. 2 mols. of the former compound to 1 to 3 mols. of the latter compound, an acidic agent to lower the pH thereof to a value of approximately 7 to approximately 9 and then to maintain the temperature of the mass between 100 DEG  and 200 DEG  F. to form the desired imidazoline. The solution of compounds of the general formulae I and II above may have a pH of at least 10 before the addition of the acidic agent. Water is given as a suitable solvent.  The preferred salts of substituted 2-imidazolines are of the general formula: <FORM:0803119/IV (b)/4> wherein X represents: <FORM:0803119/IV (b)/5> and <FORM:0803119/IV (b)/6> and R represents a hydrocarbon radical. In the examples compounds of the general formula III are prepared in which X and R represent respectively: <FORM:0803119/IV (b)/7> and C11H23- <FORM:0803119/IV (b)/8> and C11H23- <FORM:0803119/IV (b)/9> and C19H19 <FORM:0803119/IV (b)/100> and C11H23- <FORM:0803119/IV (b)/111> and C11H23- <FORM:0803119/IV (b)/122> and C17H35 <FORM:0803119/IV (b)/133> and C13H27 <FORM:0803119/IV (b)/144> and C11H23-Similar compounds to those prepared in the examples are obtainable using as the reactant of formula II a compound of the formula <FORM:0803119/IV (b)/155> to produce compounds in which R4 in the general formula above or the salts of substituted imidazolines represents an hydroxy substituted hydrocarbon group.  U.S.A. Specification 2,528,378 is referred to.