Patent GB-663745-A (GB)
Title: Aromatic and heterocyclic diazosulfones
Filed: 1948-05-24
Abstract: Aromatic and heterocyclic diazosulphones of the general formula X-R-N=N-SO2-R1 wherein R represents an aryl radical (e.g. phenyl, naphthyl, biphenyl, tolyl, salicyl, xylyl or anisyl), R1 an aminoaryl, alkoxyaryl, acylaminoaryl or heterocyclic radical (e.g. amino-, ethoxy- or acetamido-phenyl, quinolyl, carbazyl, oxazyl or indolyl) and X an arylamino (e.g. phenylamino), benzylamino, dialkylamino (e.g. diethylamino) or heterocyclic amino (e.g. morpholino, piperazino, or indolino) radical, are manufactured by reaction of a diazonium compound (prepared by diazotization of an aromatic or heterocyclic amine) or a corresponding diazocyanide or diazoamino compound, with an organic sulphinic acid (prepared by reduction of an organic sulphochloride).  The products couple with azo dye coupling components (see Group IV (c)), and yield sulphonhydrazides by reduction (e.g. with zinc and acetic acid).  In an example, p-diethylaminoaniline is diazotized and the diazo compound is reacted with 4-aminobenzenesulphinic acid to produce 4-diethylaminobenzenediazo - (p - aminophenyl) - sulphone.  A list of additional products is given. The Specification as open to inspection under Sect. 91 comprises also the manufacture of diazosulphones of the general formula above and of the general formul  <FORM:0663745/IV (b)/1> wherein R1 may additionally represent an alkyl radical (e.g. methyl, ethyl, butyl, lauryl or octadecyl) or an unsubstituted aryl radical, and X may additionally represent an amino, acylamino (e.g. acetamido, methanesulphonamido, benzamido or benzenesulphonamido) or monoalkylamino (e.g. methylamino) group, and may contain water-solubilizing substituents (e.g. sulphonic, carboxylic or polyoxyethylene groups), and wherein R2 represents a heterocyclic radical, R3 a radical of aromatic character (aryl or heterocyclic) and Z a direct carbon to carbon linkage, a bivalent hydrocarbon radical (e.g. methylene), oxygen, sulphur or an imino group; and the following additional methods of preparation: (a) oxidation of b -arylsulphonhydrazides, (b) condensation of a diazonium salt with a sulphonamide, and (c) decomposition of a diazo thiosulphonate. Additional examples and further lists of additional products are given.  This subject-matter does not appear in the Specification as accepted.ALSO:Azo dyes may be produced by coupling azo coupling components under alkaline conditions with diazosulphones of the general formula X-R-N=N-SO2-R1 wherein R represents an aryl radical, R1 an aminoaryl, alkoxyaryl, acylaminoaryl or heterocyclic radical and X an arylamino, benzylamino, dialkylamino or heterocyclic amino radical.  The Specification as open to inspection under Sect. 91 comprises also references to diazosulphones of the general formula above and of the general formul  R2-N=N-SO2-R1 and <FORM:0663745/IV (c)/1> wherein R1 may additionally represent an alkyl or an unsubstituted aryl radical, and X may additionally represent an amino, monoalkylamino or acylamino (including sulphonamido) group and may contain water-solubilizing substituents (e.g. sulpho, carboxy or polyoxyethylene groups), and wherein R2 represents a heterocyclic radical, R3 a radical of aromatic character (aryl or heterocyclic) and Z a direct carbon to carbon linkage, a bivalent hydrocarbon radical, oxygen, sulphur or an imino group.  This subject-matter does not appear in the Specification as accepted.