3,5 - Dichlorobenzene - 3 ', 5 - dichlorobenzene - 4' - methoxy salicylic anilide and 3,5 - dibromo - 3 '- chlorine - 4' - (beta - chlorine - alpha, alpha, beta - of trifluoroacetic acid ethoxy) - salicylic anilide as well as processes for their preparation

摘要

1288512 Salicylanilides and thiobenzanilides MERCK & CO Inc 7 Sept 1970 [8 Sept 1969] 42689/70 Heading C2C The invention comprises novel salicylanilides and thiobenzanilides of the formula. in which A is H, C 1-6 alkanoyl or aroyl; each of Y 1 and Y 2 is H, halogen, OH, alkyl, haloalkyl or polyhaloalkyl; Y 3 is halogen, OH, haloalkyl or polyhaloalkyl; each of X 1 and X 2 is H, halogen, alkyl, polyhaloalkyl, haloalkyl or NO 2 ; X 3 is halogen, alkyl, haloalkyl, polyhaloalkyl or NO 2 ; R 2 is H or alkyl; R 1 is alkyl, C 3-6 cyclo - alkyl or monohaloalkyl or polyhaloalkyl in which there is more than one type of halogen atom present; Z is O or S; provided that when Z is not S when R 1 is alkyl and that at least one of X 1 , X 2 , X 3 , Y 1 , Y 2 and Y 3 is other than H or halogen when R 1 is CH 3 and A is H; and all the alkyl, haloalkyl and alkoxy radicals contain not more than 5 carbon atoms, and their preparation. Compounds in which Z is O are prepared by reacting the appropriate aniline derivatives with the corresponding salicylic acids or acid halides. Compounds in which Z is S and R 2 is H are obtained by reacting phenols and phenyl isocyanates of the formulµ Compounds in which R 2 is alkyl are made by reacting the corresponding compounds in which R 2 is H with alkyl halides. The following starting materials are prepared: potassium 2,6 - dichloro - 4 - nitrophenate, potassium 2,6 - dibromo - 4 - nitrophenate, 1,3 - dichloro - 2 - methoxy - 5 - nitrobenzene, 1 - chloro - 3 - methyl - 2 - methoxy - 5 nitrobenzene, 1 - chloro - 3 - trifluoromethyl - 2- methoxy - 5 - nitrobenzene, 1,3 - dichloro - 2- cyclohexyloxy - 5 - nitrobenzene, 1,3 - dichloro- 2 - ethoxy - 5 - nitrobenzene 2 - butoxy - 1,3- dichloro - 5 - nitrobenzene, 1,3 - dibromo - 2- methoxy - 5 - nitrobenzene, 3,5 - dichloro - 4- methoxy - aniline 3,5 - dichloro - 4 - cyclohexyloxyaniline, 3,5 - dichloro - 4 - ethoxyaniline, 4 - butoxy - 3,5 - dichloroaniline, 3- chloro - 5 - ethoxy - 4 - methoxyaniline, 3- chloro - 5 - trifluoromethyl - 4 - cyclohexyloxyaniline, 3 - chloro - 5 - trifluoromethyl - 4 - ethoxyaniline, 4 - butoxy - 3 - chloro - 5 - trifluoromethylaniline, N - propyl - 3,5 - dichloro- 4 - ethoxyaniline, N isopropyl - 3,5 - dichloro- 4 - ethoxyaniline, N - butyl - 3,5 - dichloro - 4- ethoxyaniline, 3 - chloro - 4 - ethoxyphenyl isothiocyanate, 3 - chloro - 4 - cyclohexyloxyphenyl isothiocyanate, 3 - chloro - 4 - (#- chloro - ,,# - trifluoroethoxy)aniline, 1- chloro - 2 - (# - chloro - ,;# - trifluoroethoxy)- 5 - nitrobenzene and 3 - chloro - 2 - (#- chloro- ,,# - trifluoroethoxy)phenyl isocyanate. Anti-bacterial compositions contain the above novel compounds and excipients. The compounds also possess anthelminthic activity.