Patent GB-1355631-A (GB)
Title: Imidazole derivatives
IPC: C07D233/61
Filed: 1971-10-14
Abstract: 1355631 Imidazolium derivatives IMPERIAL CHEMICAL INDUSTRIES Ltd 18 Sept 1972 [14 Oct 1971] 47796/71 Heading C2C Novel imidazolium derivatives of the general formula wherein R<SP>1</SP> and R<SP>2</SP> are each a hydrogen atom or together form a fused benzene ring, R<SP>3</SP> is a C 6-14  alkyl, benzyl (having 0-5 Cl substituents in the ring) or 3-(C 4-8  alkoxy)-2-hydroxypropyl group, R<SP>4</SP> is a hydrogen atom or a C 1-3  alkyl group, (X<SP>1</SP>.X<SP>2</SP>)<SP>2(-)</SP> represents two monovalent anions or one divalent anion and A is a -(CH 2 ) n -, group, in which n is 2-12, m is 1 or 2, p is 0, 1 or 2, r is 1-4 and Z is a phenylene, naphthylene or phenylenedioxy group each optionally substituted by chlorine atoms or methoxy or methyl groups or a C 2-12  alkylenedioxy group, are prepared (a) by treating an imidazole of the general formula with at least one compound of the general formula R<SP>3</SP>Y<SP>1</SP>, R<SP>3</SP>Y<SP>2</SP> or R<SP>3</SP> 2 (Y<SP>1</SP>.Y<SP>2</SP>); (b) when X<SP>1</SP> and X<SP>2</SP> are monovalent anions, by treating a compound of the general formula with a compound of the general formula R<SP>3</SP>Y<SP>1</SP>; (c) when X<SP>1</SP> and X<SP>2</SP> are monovalent anions, by treating an imidazole of the general formula with a quaternizing agent of the general formula Y<SP>1</SP>-A-Y<SP>2</SP>; (d) when X<SP>1</SP> and X<SP>2</SP> are monovalent anions, by treating a compound of the eighth general formula above with an imidazole of the general formula and (e) by metathetically reacting a compound of the general formula with a salt of the general formula D<SP>(+)</SP>(X<SP>5</SP>)<SP>(-)</SP>, D<SP>(+)</SP>(X<SP>6</SP>)<SP>(-)</SP>, D 2 <SP>(+)</SP>.(X<SP>5</SP>.X<SP>6</SP>)<SP>2(-)</SP> or B<SP>2(+)</SP>.(X<SP>5</SP>.X<SP>6</SP>)<SP>2(-)</SP> wherein Y<SP>1</SP> and Y<SP>2</SP> are the same or different monovalent radicals and Y<SP>1</SP>.Y<SP>2</SP> is a divalent radical, derived from acids HY<SP>1</SP>, HY<SP>2</SP> and H 2 Y<SP>1</SP>.Y<SP>2</SP>, respectively, having pK values of less than 2 and (X<SP>5</SP>.X<SP>6</SP>)<SP>2(-)</SP> and (X<SP>3</SP>.X<SP>4</SP>)<SP>2(-)</SP> are different groups of two monovalent anions or a divalent anion falling within the definition of (X<SP>1</SP>.X<SP>2</SP>)<SP>2(-)</SP>, D<SP>(+)</SP> is a mono-valent cation and B<SP>2(+)</SP> is a divalent cation. Imidazoles of the eighth general formula above are prepared by reacting the corresponding compound in which R<SP>3</SP> is a hydrogen atom with a compound of the general formula R<SP>3</SP>Br. Quaternizing agents of the ninth general formula above wherein Y<SP>1</SP> and Y<SP>2</SP> are chlorine atoms and A is a group are prepared by reacting a diamine of the general formula with a compound of the general formula Cl(CH 2 ) m CO 2 CH 3  or ClCH 2 CO 2 CH 3 , respectively. Imidazoles of the second general formula above are prepared by reacting an imidazole of the eighth general formula above wherein R<SP>3</SP> is a hydrogen atom with a compound of the general formula Cl-A-Cl. Antibacterial, antiseptic and disinfectant compositions comprise, as active ingredient, an imidazolium derivative of the first general formula above, together with an inert diluent or carrier.