Hoechst Aktiengesellschaft

Werner Brodt

Theodor Papenfuhs

Hermann Fuchs

Folker Kohlhaas

Process for the preparation of N-alkylhalogenoanilines

Compounds of the formula (1) ##STR1## in which X denotes a sulfur atom or the group ##STR2## in which R denotes a hydrogen atom, an alkylene-C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.6 - or alkyl-C.sub.1 -C.sub.6 - group, each of which can be substituted by hydroxyl, sulfo, carboxyl or cyano groups, R.sub.1 denotes a hydrogen atom or an alkyl-C.sub.1 -C.sub.6 -group which can be substituted by --SO.sub.3 M or COOM groups (where M denotes an H, Li, Na, K or Ca atom), hydroxyl, amino, methylamino, acetylamino, alkyl-C.sub.1 -C.sub.4 -sulfonylamino, methoxy, ethoxy, .beta.-hydroxyethylsulfonyl, phenyl, monosulfophenyl, disulfophenyl, or 4-[.beta.-hydroxyethylsulfonyl]-2-sulfophenyl groups, or represents a phenyl or naphthyl group, each of which can be substituted by --SO.sub.3 M or COOM groups (where M denotes an H, Li, Na, K or Ca atom), alkyl-C.sub.1 -C.sub.4 -, alkoxy-C.sub.1 -C.sub.4 -, amino, methylamino, alkyl-C.sub.1 -C.sub.4 -sulfonylamino or acetylamino groups, and R.sub.2 is hydrogen or oxygen, and process for their preparation by reacting compounds of the formula (2) ##STR3## in which Y denotes a chlorine or bromine atom, with a compound of the formula (3)

Substituted phenyl hydroxyethyl sulfones, and process for their

A process for the preparation of arylaminonitrophenyl hydroxyethyl sulfones of the formula (1) ##STR1## in which Z denotes the radical ##STR2## in which R.sub.1 denotes a hydrogen atom or an --NH.sub.2, --NH--R or --N(R).sub.2 group, R representing a C.sub.1 -C.sub.4 -alkyl group, R.sub.2 denotes a hydrogen atom, a C.sub.1 -C.sub.4 -alkyl group or a C.sub.1 -C.sub.4 -alkoxy group, R.sub.3 represents a hydrogen, chlorine or bromine atom or a sulfonic acid, sulfonamide, carboxylic acid, carboxamide, hydroxyl, carbomethoxy, carboethoxy or hydroxyethylsulfonyl group, R.sub.4 denotes a hydrogen, chlorine or bromine atom or a sulfonic acid, carboxylic acid, hydroxy or C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkyl group, it being possible for 1-3 different R.sub.1 -R.sub.3 substituents, not more than two of which may, however, be identical, to be present in the radical Z.sub.a, and for 1-4 different R.sub.1 -R.sub.4 -substituents, not more than two of which may, however, be identical, to be present in the radical Z.sub.b, and R has the meaning mentioned earlier in the text, which comprises reacting compounds of the formula (2) ##STR3## in which X denotes a chlorine or bromine atom, with an amino compound of the formula ##STR4## in which R, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 have the said meanings, at 20.degree. to 180.degree. C., at pH values from 4.0 to 10.0 in water or in suitable organic solvents and in the presence of an inorganic or organic acid-binding agent.

Arylaminonitrophenyl hydroxyethyl sulfones

Process for the preparation of 2-nitro-4-sulfamyldiphenylamine dyestuffs of the formula (1) ##STR1## in which R.sub.1 and R.sub.2 each denote a hydrogen, chlorine or bromine atom or a C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy group or a phenoxy group which can be substituted on the benzene nucleus by chlorine or bromine atoms or C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or trifluoromethyl groups, or denote a naphthoxy group, and R.sub.2 can also be an -N-(C.sub.1 -C.sub.4 -alkyl).sub.2, -NH-(C.sub.1 -C.sub.4 -alkyl), -NH-(C.sub.1 -C.sub.4 -alkanoyl) or -NH-benzoyl group, and R.sub.3 and R.sub.4 each denote a hydrogen atom or a C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.2 -alkoxy-C.sub.1 -C.sub.4 -alkyl or C.sub.5 -C.sub.6 -cycloalkyl group, and R.sub.4 can also be a phenyl group which can be substituted by chlorine or bromine atoms or C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, -N-(C.sub.1 -C.sub.4 -alkyl).sub.2, -NH-(C.sub.1 -C.sub.4 -alkyl), -NH-(C.sub.1 -C.sub.4 -alkanoyl), -NH-benzoyl, phenoxy or naphthoxy groups, by sulfonating o-nitrochlorobenzene with chlorosulfonic acid at 100.degree.-110.degree. C. to give 4-chloro-3-nitrobenzenesulfonic acid of the formula (2) ##STR2## converting the latter by means of thionyl chloride at 70.degree.-80.degree. C. into 4-chloro-3-nitrobenzenesulfochloride, precipitating the latter on ice and subjecting the resulting 4-chloro-3-nitrobenzenesulfochloride to a condensation reaction first with an aliphatic or aromatic amine of the formula ##STR3## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4 have the meanings mentioned, suspended or dissolved in an aqueous solution of a basic condensation agent, the presence of an ionic or nonionic surfactant, initially at 5.degree. to 50.degree. C. and at pH 7.5 to 12.5, and then with an aromatic amine of the formula (4) mentioned, suspended or dissolved in an aqueous solution of a basic condensation agent, at 80.degree. to 100.degree. C., within the pH range mentioned and in the presence of a surfactant of the type mentioned.

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