Process for the production of azo compounds
AssigneeSandoz Ltd.
InventorPeter Matzinger
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Abstract
Process for the production of triazoles of the formula ##STR1## in which R.sub.1 is hydrogen or an aliphatic or aromatic substituent conventional for diazo components of disperse dyes, which substituent is bound to the N-atom in the 1- or 2-position of the triazole nucleus through a carbon atom, and K is a coupling component radical comprising treating a compound of the formula ##STR2## with a dehydrating agent.
Claims20
A process for the synthesis of a compound of the formula ##STR10## comprising treating a compound of the formula ##STR11## with a dehydrating agent to obtain a compound of the formula ##STR12## said dehydrating agent being an agent capable of dehydrating a compound of the formula ##STR13## to a compound of the formula ##STR14## wherein R.sub.1 is hydrogen;
- C.sub.1-4 alkyl;
- C.sub.1-4 alkyl monosubstituted by fluoro, chloro, bromo, (C.sub.1-4 alkyl)carbonyl, C.sub.1-4 alkoxy, cyano, thiocyano, phenoxy, (C.sub.1-4 -alkoxy)carbonyl, phenoxycarbonyl, (C.sub.1-4 alkoxy)-ethoxycarbonyl, (C.sub.1-4 alkyl)carbamoyl, di-(C.sub.1-4 -alkyl)carbamoyl, phenylcarbamoyl, N-C.sub.1-4 alkyl-N-phenylcarbamoyl, benzoyl, (C.sub.1-4 alkyl)carbonyloxy, phenylsulfonyl, C.sub.1-4 alkylsulfonyl, sulfamoyl, C.sub.1-4 alkylsulfamoyl, di-(C.sub.1-4 alkyl)sulfamoyl, phenylsulfamoyl, N-C.sub.1-4 alkyl-N-phenylsulfamoyl, phenyl or substituted phenyl having 1 or 2 substituents each of which is independently chloro, bromo, nitro, cyano, trifluoromethyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy;
- C.sub.2-4 alkenyl;
- C.sub.2-4 alkenyl monosubstituted by chloro, bromo or phenyl;
- C.sub.2-4 alkynyl;
- phenyl or substituted phenyl having 1 to 3 substituents each of which is independently C.sub.1-4 alkyl, C.sub.1-4 alkoxy, chloro, bromo, nitro, cyano (maximum of two), trifluoromethyl (maximum of two), (C.sub.1-4 alkoxy)carbonyl (maximum of two), formyl (maximum of one), (C.sub.1-4 -alkyl)carbonyl (maximum of one), (C.sub.-4 alkyl)carbamoyl (maximum of one), di-(C.sub.1-4 alkyl)carbamoyl (maximum of one), C.sub.1-4 alkylsulfonyl (maximum of one), phenylsulfonyl (maximum of one), sulfamoyl (maximum of one), C.sub.1-4 -alkylsulfamoyl (maximum of one), di-(C.sub.1-4 alkyl)sulfamoyl (maximum of one) or phenylsulfamoyl (maximum of one), with the proviso that R.sub.1 is in the 1-position of the triazole ring and the broken line represents double bonds in the 2,3- and 4,5-positions or R.sub.1 is in the 2-position of the triazole ring and the broken line represents double bonds in the 3,4- and 1,5-positions, and
- K is a coupling component radical.
A process for the synthesis of a compound of the formula ##STR18## comprising diazotizing a compound of the formula ##STR19## coupling the resulting diazonium compound with a compound of the formula H-K to form an azo compound of the formula ##STR20## and treating said azo compound with a dehydrating agent to obtain a compound of the formula ##STR21## said dehydrating agent being an agent capable of dehydrating a compound of the formula ##STR22## to a compound of the formula ##STR23## wherein R.sub.1 is hydrogen;
- C.sub.1-4 alkyl;
- C.sub.1-4 alkyl monosubstituted by fluoro, chloro, bromo, (C.sub.1-4 alkyl)carbonyl, C.sub.1-4 alkoxy, cyano, thiocyano, phenoxy, (C.sub.1-4 -alkoxy)carbonyl, phenoxycarbonyl, (C.sub.1-4 alkoxy)-ethoxycarbonyl, (C.sub.1-4 alkyl)carbamoyl, di-(C.sub.1-4 -alkyl)carbamoyl, phenylcarbamoyl, N-C.sub.1-4 alkyl-N-phenylcarbamoyl, benzoyl, (C.sub.1-4 alkyl)carbonyloxy, phenylsulfonyl, C.sub.1-4 alkylsulfonyl, sulfamoyl, C.sub.1-4 alkylsulfamoyl, di-(C.sub.1-4 alkyl)sulfamoyl, phenylsulfamoyl, N-C.sub.1-4 alkyl-N-phenylsulfamoyl, phenyl or substituted phenyl having 1 or 2 substituents each of which is independently chloro, bromo, nitro, cyano, trifluoromethyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy;
- C.sub.2-4 alkenyl;
- C.sub.2-4 alkenyl monosubstituted by chloro, bromo or phenyl;
- C.sub.2-4 alkynyl;
- phenyl or substituted phenyl having 1 to 3 substituents each of which is independently C.sub.1-4 alkyl, C.sub.1-4 alkoxy, chloro, bromo, nitro, cyano (maximum of two), trifluoromethyl (maximum of two), (C.sub.1-4 alkoxy)carbonyl (maximum of two), formyl (maximum of one), (C.sub.1-4 -alkyl)carbonyl (maximum of one), (C.sub.1-4 alkyl)carbamoyl (maximum of one), di-(C.sub.1-4 alkyl)carbamoyl (maximum of one), C.sub.1-4 alkysulfonyl (maximum of one), phenylsulfonyl (maximum of one), sulfamoyl (maximum of one), C.sub.1-4 -alkylsulfamoyl (maximum of one), di-(C.sub.1-4 alkyl)sulfamoyl (maximum of one) or phenylsulfamoyl (maximum of one), with the proviso that R.sub.1 is in the 1-position of the triazole ring and the broken line represents double bonds in the 2,3- and 4,5-positions or R.sub.1 is in the 2-position of the triazole ring and the broken line represents double bonds in the 3,4- and 1,5-positions, and
- K is a coupling component radical.
Dependencies are inferred from the claim text.