2-Optionally substituted alkyl-and phenylsulfonylphenyl-azo-phenyl dyes and a process for their synthesis

A compound of the formula ##STR89## wherein R.sub.11 is lower alkyl, substituted lower alkyl, phenyl or substituted phenyl, wherein the substituent of substituted lower alkyl is chloro or bromo and each substituent of substituted phenyl is independently fluoro, chloro, bromo, iodo, hydroxy, methyl, amino, methylamino, nitro or acetamido,

• R.sub.12 is hydrogen, lower alkyl, formamido, substituted lower alkylcarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, benzamido, methylsulfonylamino or ethylsulfonylamino, wherein the substituent of substituted lower alkylcarbonylamino is chloro, bromo, acetoxy, methoxy, ethoxy or phenoxy,
• R.sub.13 is hydrogen, lower alkyl or lower alkoxy,
• R.sub.14 is hydrogen, lower alkyl or substituted lower alkyl wherein the substituent is cyano, hydroxy, methoxy, ethoxy, cyanoethoxy, formyloxy, acetoxy, propionyloxy, methoxycarbonyl, ethoxycarbonyl, methoxycarbonyloxy, ethoxycarbonyloxy, acetoxyethoxy or phenyl, and
• R.sub.15 is hydrogen, lower akyl or substituted lower alkyl wherein the substituent is hydroxy, methoxy, ethoxy, cyanoethoxy, phenoxy, phenyl, methylamino, ethylamino, formyloxy, acetoxy, propionyloxy, benzoyloxy, methoxycarbonyl, ethoxycarbonyl, phenoxycarbonyl, methoxycarbonyloxy, ethoxycarbonyloxy, phenoxycarbonyloxy, methoxyethoxycarbonyl, 1,1-dimethylhydrazinium A.sup.-, trimethylammonium A.sup.-, or triethylammonium A.sup.-, wherein A.sup.- is an anion.

A compound of the formula ##STR90## wherein R.sub.11 is lower alkyl, substituted lower alkyl, phenyl or substituted phenyl, wherein the substituent of substituted lower alkyl is chloro or bromo and each substituent of substituted phenyl is independently fluoro, chloro, bromo, iodo, hydroxy, methyl, amino, methylamino, nitro or acetamido,

• R.sub.12 is hydrogen, lower alkyl, formamido, lower alkylcarbonylamino, substituted lower alkylcarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, benzamido, methylsulfonylamino or ethylsulfonylamino, wherein the substituent of substituted lower alkylcarbonylamino is chloro, bromo, acetoxy, methoxy, ethoxy or phenoxy,
• R.sub.13 is lower alkyl or lower alkoxy,
• R.sub.14 is hydrogen, lower alkyl or substituted lower alkyl wherein the substituent is cyano, hydroxy, methoxy, ethoxy, cyanoethoxy, formyloxy, acetoxy, propionyloxy, methoxycarbonyl, ethoxycarbonyl, methoxycarbonyloxy, ethoxycarbonyloxy, acetoxyethoxy or phenyl, and
• R.sub.15 is hydrogen, lower alkyl or substituted lower alkyl wherein the substituent is hydroxy, methoxy, ethoxy, cyanoethoxy, phenoxy, phenyl, methylamino, ethylamino, formyloxy, acetoxy, propionyloxy, benzoyloxy, methoxycarbonyl, ethoxycarbonyl, phenoxycarbonyl, methoxycarbonyloxy, ethoxycarbonyloxy, phenoxycarbonyloxy, methoxyethoxycarbonyl, 1,1-dimethylhydrazinium A.sup.-, trimethylammonium A.sup.-, or triethylammonium A.sup.-, wherein A.sup.- is an anion.

A compound of the formula ##STR91## wherein R.sub.11 is lower alkyl, substituted lower alkyl, phenyl or substituted phenyl, wherein the substituent of substituted lower alkyl is chloro or bromo and each substituent of substituted phenyl is independently fluoro, chloro, bromo, iodo, hydroxy, methyl, amino, methylamino, nitro or acetamido,

• R.sub.12 is hydrogen, lower alkyl, formamido, lower alkylcarbonylamino, substituted lower alkylcarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, benzamido, methylsulfonylamino or ethylsulfonylamino, wherein the substituent of substituted lower alkylcarbonylamino is chloro, bromo, acetoxy, methoxy, ethoxy or phenoxy,
• R.sub.13 is hydrogen, lower alkyl or lower alkoxy,
• R.sub.14 is hydrogen or substituted lower alkyl wherein the substituent is cyano, hydroxy, methoxy, ethoxy, cyanoethoxy, formyloxy, acetoxy, propionyloxy, methoxycarbonyl, ethoxycarbonyl, methoxycarbonyloxy, ethoxycarbonyloxy, acetoxyethoxy or phenyl, and
• R.sub.15 is hydrogen, lower alkyl or substituted lower alkyl wherein the substituent is hydroxy, methoxy, ethoxy, cyanoethoxy, phenoxy, phenyl, methylamino, ethylamino, formyloxy, acetoxy, propionyloxy, benzoyloxy, methoxycarbonyl, ethoxycarbonyl, phenoxycarbonyl, methoxycarbonyloxy, ethoxycarbonyloxy, phenoxycarbonyloxy, methoxyethoxycarbonyl, 1,1-dimethylhydrazinium A.sup.-, trimethylammonium A.sup.-, or triethylammonium A.sup.-, wherein A.sup.- is an anion.

A compound of the formula ##STR92## wherein R.sub.11 is lower alkyl, substituted lower alkyl, phenyl or substituted phenyl, wherein the substituent of substituted lower alkyl is chloro or bromo and each substituent of substituted phenyl is independently fluoro, chloro, bromo, iodo, hydroxy, methyl, amino, methylamino, nitro or acetamido,

• R.sub.12 is hydrogen, lower alkyl, formamido, lower alkylcarbonylamino, substituted lower alkylcarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, benzamido, methylsulfonylamino or ethylsulfonylamino, wherein the substituent of substituted lower alkylcarbonylamino is chloro, bromo, acetoxy, methoxy, ethoxy or phenoxy,
• R.sub.13 is hydrogen, lower alkyl or lower alkoxy,
• R.sub.14 is hydrogen, lower alkyl or substituted lower alkyl wherein the substituent is cyano, hydroxy, methoxy, ethoxy, cyanoethoxy, formyloxy, acetoxy, propionyloxy, methoxycarbonyl, ethoxycarbonyl, methoxycarbonyloxy, ethoxycarbonyloxy, acetoxyethoxy or phenyl, and
• R.sub.15 is hydrogen or substituted lower alkyl wherein the substituent is hydroxy, methoxy, ethoxy, cyanoethoxy, phenoxy, phenyl, methylamino, ethylamino, formyloxy, acetoxy, propionyloxy, benzoyloxy, methoxycarbonyl, ethoxycarbonyl, phenoxycarbonyl, methoxycarbonyloxy, ethoxycarbonyloxy, phenoxycarbonyloxy, methoxyethoxycarbonyl, 1,1-dimethylhydrazinium A.sup.-, trimethylammonium A.sup.-, or triethylammonium A.sup.-, wherein A.sup.- is an anion.

A compound of the formula ##STR93## wherein R.sub.11 is methyl, ethyl, bromomethyl, phenyl, 4-bromophenyl, 4-fluorophenyl, 4-iodophenyl, 2-methylphenyl, 4-methylphenyl, 3-nitrophenyl, 4-acetamido-3-chlorophenyl, 3-amino-6-chlorophenyl, 4-chloro-3-methylphenyl, 4-chloro-3-methylaminophenyl, 2-chloro-4-nitrophenyl, 4-chloro-3-nitrophenyl, 3,4-dichlorophenyl, 2-hydroxy-5-nitrophenyl or 2-methyl-5-nitrophenyl,

• R.sub.12 is hydrogen, methyl, ethyl, formamido, acetamido, propionamido, methoxyacetamido, ethoxyacetamido, phenoxyacetamido, acetoxyacetamido, methoxypropionamido, ethoxypropionamido, methoxycarbonylamino, ethoxycarbonylamino, benzamido, methylsulfonylamino or ethylsulfonylamino,
• R.sub.13 is hydrogen, methyl, ethyl, methoxy or ethoxy,
• R.sub.14 is methyl, ethyl, butyl, .beta.-substituted ethyl wherein the substituent is cyano, methoxy, formyloxy, acetoxy, propionyloxy, methoxycarbonyl, ethoxycarbonyl, methoxycarbonyloxy or 2-acetoxyethoxy or 3-acetoxypropyl, and
• R.sub.15 is hydrogen, methyl, ethyl, propyl, benzyl, .beta.-substituted ethyl wherein the substituent is hydroxy, methoxy, 2-cyanoethoxy, phenoxy, phenyl, formyloxy, acetoxy, propionyloxy, benzoyloxy, methoxycarbonyl, ethoxycarbonyl, phenoxycarbonyl, methoxycarbonyloxy, ethoxycarbonyloxy, phenoxycarbonyloxy or 2-methoxyethoxycarbonyl or 3-acetoxypropyl,
• with the proviso that when R.sub.11 is methyl, R.sub.12 is acetamido and R.sub.13 is hydrogen, at least one of R.sub.14 and R.sub.15 is other than ethyl.