Verfahren zur Herstellung neuer Benzolsulfonylharnstoffe und deren Salzen

摘要

Novel benzenesulphonyl ureas of the formula wherein A is an alkyl, aryl or alkoxy-, alkyl-or halogen-substituted aryl radical, X is an alkylene or alkenylene radical and R is an alkyl, aralkyl, cycloalkyl (which may bear alkyl or alkoxy substituents or a heterocyclic radical) and salts thereof, are made by reacting a benzenesulphonyl compound A.CO.X.C6H4.SO2.Z with a compound of the formula R-U, in which one of the symbols Z and U represents an amino group and the other represents an isocyanate group or a group convertible to isocyanate under the reaction conditions. p - (b - Benzoylvinyl) - benzenesulphonamide, p - (g - benzoylpropyl) - benzenesulphonamide, p - (d - benzoylbutyl) - benzenesulphonamide, p-[g - (p - chlorobenzoyl) - propyl] - benzenesulphonamide, p - [g - (p - toluyl) - propyl] - benzenesulphonamide, p - [g - (b - naphthoyl) - propyl]-benzenesulphonamide and p - [g - (a - naphthoyl)-propyl] - benzenesulphonamide are made by treating the corresponding sulphonyl chlorides (obtained from the appropriate amine by diazotization and Meerwein-Sandmeyer reaction) with ammonia. Other intermediate compounds include b - benzoyl - p - nitrostyrene, b - benzoyl-p - aminostyrene, p - (b - benzoylethyl) - benzenesulphonamide, p - nitrophenylethyl bromide, p-nitrophenylethyl - malonic acid diethyl ester, g - p - nitrophenylbutyric acid and the corresponding acid chloride, a -(p-nitrophenylethyl)-acetophenone, a - (p - aminophenylethyl) - acetophenone, 4 - (21 - chlorobutan - 31 - on - 11 - yl)-benzenesulphonamide, 4 - (butan - 31 - on - 11 - yl) - benzenesulphonamide, p - (d - benzoylbutyl)-aniline, p - [g - (p - chlorobenzoyl) - propyl]-nitrobenzene, p - [g - (p - chlorobenzoyl) - propyl]-nitrobenzene, p - [g - (p - chlorobenzoyl) - propyl]-aniline, p - (g - p - toluyl - propyl) - nitrobenzene, p-(g - p - toluyl - propyl) - aniline, p - [g - (a -and b -) - naphthoyl - propyl] - nitrobenzenes, p-[g - (a and b ) - naphthoyl - propyl] - anilines and ethyl benzenesulphonyl urethanes bearing a substituent A-CO-X- on the benzene residue.