Patent GB-706421-A (GB)
Title: Improvements in or relating to process for preparing quaternary ammonium compounds
IPC: C07C275/30
Filed: 1951-04-11
Abstract: The invention comprises compounds of the formula <FORM:0706421/IV (b)/1> where the alkyl radicals together contain 2-6 carbon atoms, Y and Z are hydrogen, halogen or trifluoromethyl (not both hydrogen) and X is one of the following linkages: -CH2-, -CH2-CO-NH-, -CH2-CH2-CO-NH-, -CH2-CH2-O-CO-NH-, -CH2-CH2-NH-SO2-, -CH2-CH2 CH2-NH-CO-, -CH2-CO-O-, -CH2-CO, or -CH2-CH2-NH-CO-NH-.  These are made by treating chloracetamides of the formula Hal-CH2-CO-NH-C6H3Z(CF3) with secondary aliphatic amines to give substituted glycinamides and quaternating the latter with Hal-X-C6H3YZ.  Ethyl acetate is the preferred solvent.  An alternative method of preparation is from the above chloracetamides and (alkyl)2N-X-C6H3YZ.  The quarternary halides may be converted into other salts, e.g. by double decomposition.  In the examples, (1) dimethylaminoaceto-3- trifluoromethyl - 4 - chloranilide is reacted with 4-chlorobenzyl chloride, 3:4-dichlorobenzyl chloride, chloroaceto-3-trifluoromethyl-4-chloroanilide, 4-chlorophenacyl chloride, 4-chloro-phenylcarbamic b -chloroethyl ester, 3-trifluoromethyl-phenylcarbamic b -chloroethyl ester, chloroaceto-2-chloro-5-trifluoromethylanilide, chloroaceto-2:4:5-trichloroanilide and chloroacetic 3-methyl-4-chlorophenyl ester; (2) dimethylaminoaceto-3-trifluoromethylanilide is reacted with chloroaceto-4-chloroanilide and 3-trifluoromethyl-4-chlorophenylcarbamic b -chloroethyl ester; (3) dimethylaminoaceto - 3:5 - bis - trifluoromethyl - anilide is heated with 4-chlorobenzyl chloride and 3:4-dichlorobenzyl chloride; (4) diethylaminoaceto-3-trifluoromethyl-4-chloranilide is reacted with chloroaceto-3:4-dichloroanilide; (5) diethylaminoaceto-3-trifluoromethyl-anilide is reacted with chloroaceto-3-trifluoromethyl-4-chloroanilide; (6) chloroaceto-3-trifluoromethyl-4-chloroanilide is reacted with 4-chlorophenylcarbamic b -dimethylaminoethyl ester, 3-trifluoromethylphenylcarbamic b -dimethylaminoethyl ester, 1-dimethylamino-3-(31:41-dichlorobenzoylamino)-propane and N-(3:4 - dichlorophenyl)- N1 - (b  - dimethylamino - ethyl)-urea; (7) chloroaceto-3-trifluoromethylanilide is reacted with 3-trifluoromethyl-4-chlorophenylcarbamic b -dimethylaminoethyl ester and N:N-dimethyl-N1-(3-trifluoromethyl-4-chlorobenzenesulphonyl) -ethylene diamine; (8) dimethylaminoaceto-2-chloro-5-trifluoromethylanilide is heated with chloroacetyl-4-chloroanilide and chloroacetyl-3-trifluoromethyl-4-chloroanilide; (9) dimethylaminoaceto-4-trifluoromethylanilide is reacted with 3:4-dichlorobenzyl chloride, chloroacetyl-3:4-dichloroanilide and chloroacetyl-3-trifluoromethyl-4-chloroanilide.  Other products obtained similarly are those from diethylaminoaceto-3-trifluoromethyl-4-chloroanilide and the corresponding dipropylamino compound by reaction with chloroaceto-4-chloroanilide.  The following amines are condensed first with chloroacetyl chloride to give chloroacetamides and then with dimethylamine to yield dimethylamino-acetamides: 3-trifluoromethyl-4-chloroaniline, 3-trifluoromethylaniline and 2-chloro-5-trifluoromethyl-aniline.  N:N-dimethyl- N1 - (3-trifluoromethyl-4-chlorobenzenesulphonyl)-ethylene diamine is made from 3 - trifluoromethyl - 4 - chlorobenzenesulphonyl chloride and N:N-dimethyl-ethylenediamine.  - Dimethylamino - 3 - (31: 41 - dichlorobenzoyl - amino)-propane is prepared from 3:4-dichlorobenzoyl chloride and 3-dimethylamino-propylamine.