Patent GB-592875-A (GB)
Title: Method of producing organometallic compounds containing 1,3,5-triazine rings
IPC: C07F9/92
Filed: 1945-05-18
Abstract: 1 : 3 : 5-Triazine compounds of the general formula <FORM:0592875/IV/1> where X and Y represent the same or different halogen, amino or alkylamino radicals, A and B represent hydrogen or a hydroxyl group and may be different, and D represents oxygen, dihalogen, the group <FORM:0592875/IV/2> where A, B, X and Y have the above significance, or the group =(SR)2, where -SR is the residue of a sulphydril compound of the type HS-R, where R represents aliphatic or cyclic radicals, are prepared by subjecting a triazinyl-aminophenyl-stibinic acid compound to the action of a reducing agent consisting of stannous chloride sulphur dioxide, hypophosphorus acid, sodium hydrosulphite or a compound of the general formula RSH, where R has the above significance, e.g. thioglycollic, thioacetic, thiopropionic, thiobenzoic, thiosalicylic, p-sulphydrilbenzene sulphonic and p-sulphydril-phenylacetic acids, cysteine, glutathione, thiophenol, thioacetamide, thioglycollamide, 8-mercaptoquinoline and 2-mercaptopyridine.  In examples: (1) 2 : 4 - diamino - 1 : 3 : 5 - triazine - 6 - aminophenyl-(21-hydroxy-51-stibine dichloride) is prepared by reacting 2 : 4-dichloro-1 : 3 : 5-triazine-6-aminophenyl-(21-hydroxy-51-stibinic acid) with ammonia and then reducing with stannous chloride and hydrochloric acid; (2) 2 : 4-diamino-1 : 3 : 5-triazine-6-aminophenyl-(21-amino-41-stibine dichloride) is prepared by reducing 2 : 4-diamino-1 : 3 : 5-triazine-6-aminophenyl-(21-nitro-41-stibinic acid) with stannous chloride and hydrochloric acid; (3) the hydrochloride of 2 : 4-diamino-1 : 3 : 5-triazine-6-p-aminophenyl stibine dichloride is prepared by reducing p - (2 : 4 - diamino - 1 : 3 : 5 - triazinyl - (6))-aminophenyl stibinic acid with sulphur dioxide in the presence of hydrochloric and hydriodic acids, and is converted to p-(2 : 4-diamino-1 : 3 : 5-triazinyl-(6))-aminophenylstibine oxide by the action of ammonia; (4) (2 : 4-diamino-1 : 3 : 5-triazinyl-(6))-p-aminophenyl-stibinoso-dithioglycollic acid is prepared by reacting (2 : 4-diamino-1 : 3 : 5-triazine-(6))-p-aminophenyl-stibinic acid dissolved in aqueous potash with thioglycollic acid.  p,p1-1 : 3 : 5-Triazinyl - 6 - aminostibinobenzene compounds are prepared by reducing a 1 : 3 : 5-triazinylaminophenyl stibinic acid compound, for example, with stannous chloride or hypophosphorus acid in hydrochloric acid solution in the presence of hydriodic acid, or sodium hydrosulphite in alkaline solution.  Specification 585,678 is referred to.  The Specification as open to inspection under Sect. 91 refers generally to the preparation of 1 : 3 : 5-triazine compounds of the above general formula by similar methods, where A and B may be the same or different and represent hydrogen, halogen, nitro, hydroxyl, alkoxy, amino, substituted amino or alkyl radicals, D represents oxygen, sulphur, dihalides, radicals of the formula <FORM:0592875/IV/3> and sulphur containing groups of the type = (SR)2, where -SR is the residue of a sulphydril compound of the type HS-R, where R represents aliphatic or cyclic radicals, and X and Y may be the same or different and may represent halogen or residues of any inorganic or organic substituted or unsubstituted aliphatic, cyclic, isocyclic, heterocyclic, monocyclic or polycyclic molecules containing an active hydrogen atom capable of reacting with a cyanuric halide with the formation of hydrogen halide, for example, X and Y may represent the radicals -Cl, -Br, -I, -F, -H, -OH, -O-Alkyl, -O-Acyl, -NH2, -NH-Alkyl, -N-(Alkyl)2, -NH-Acyl, -NHNH2, -NHNH-Alkyl, -N-Alkyl-NH2, -N-Alkyl-NH-Alkyl, -NHNH-Acyl, -N-Acyl-NH2, -N-Acyl-NH-Acyl, -NH-Aryl, -NH(CH2)nCONH2, -NH(CH2)nNH2, -NH(CH2)nNH-Alkyl, -NH(CH2)n-di-Alkyl, -NH(CH2)nOH, -NHCH2CHOH <FORM:0592875/IV/4> <FORM:0592875/IV/5> , residues of cyanamide derivatives or substituted guanidines, amino derivatives of carbohydrates particularly of monosaccharides such as glucose amine, -SH, -SR, where R has the significance indicated above, and substituted aryl radicals such as those corresponding to the formul  -NHC6H2(A, B, E) and -NHNHC6H2(A, B, E) where A and B have the significance indicated above and E represents -SO3H, -SO2NH2 or -COOH which may be in the ortho-, meta- or para-position to the -NH- or NHNH-group.  X and/or Y may also represent <FORM:0592875/IV/6> where M represents hydrogen or salt forming atoms or radicals, <FORM:0592875/IV/7> where A, B and D have the significance indicated above, or 1 : 3 : 5-triazine groups or residues, and any one of these radicals, triazine groups or residues may be linked directly or indirectly to the ring carbon atoms of the triazine ring in the general formula.  In the latter case, the link may be formed by a cyclic or aliphatic amine radical, for example, by an -NH-Aryl, -NH-Alkyl, -NHNH-Aryl or -NHNH-Alkyl radical and when X and/or Y represents a triazine ring the link may be formed by an -NH-, -NHNH-, or an aliphatic or cyclic diamine, for example, of the formula -NHC6H4NH- or -NHCH2CH2NH-.  This subject-matter does not appear in the Specification as accepted.