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United States Patent Office Patented Sept 3,053,843 United States Patent Office Patented Sept. 11, 1962 2 chloride in inert organic solvents such as hydrocarbons, 3,053,843 in the presence of hydrogen chloride and of dialkyl ethers NEW CONDENSATON PRODUCTS DERVED or dialkylamides of lower fatty acids, possibly under pres FROM TETRAMERIC CYANOGEN HALDES Hans Gysin, Basel, Enrico Kaisli, Riehen, near Basel, and Sure. It is obtained, together with trimeric crystalline Jirg Rumpf, Binningen, near Basel, Switzerland, as cyanuric chloride, as an oily liquid which, after removal signors to J. R. Geigy A.G., Basel, Switzerland - of the organic solvent (which can be used again), is easily No Drawing. Filed July 11, 1960, Ser. No. 41,798 separated by distillation. Pure tetrameric cyanogen chlo Claims priority, application Switzerland Sept. 28, 1959 ride is a water-clear, oily liquid; its density is do. 1.681, 8 Claims. (C. 260-249.5) its refraction index is no=1.5759 and it can be distilled 10 without decompositoin at 126 C. under 14 mm. Hg pres The present invention concerns a process for the pro Sure. Elementary analysis corresponds to the formula duction of new condensation products as well as the com CANaCl4. On hydrolysing in water at 20° C., a quanti pounds obtained by this process which can be used in tative yield of 2-amino-4,6-dichloro-1,3,5-triazine is ob many ways as described in detail below. tained therefrom while 1 mol of carbon dioxide and 2 It has been found that valuable new condensation 15 mols of hydrogen chloride are split off. On hydrolysing products are obtained if tetrameric cyanogen halides of in water at 100° C., 2,4,6-trihydroxy-1,3,5-triazine (cy the formula CNHall having the structural Formula I anuric acid) is obtained therefrom while 1 mol of carbon dioxide, 4 mols of hydrogen chloride and 1 mol of am Hal monia are split off. This chemical behaviour indicates 20 the accuracy of the Formulae I and II and shows that tetrameric cyanogen chloride contains 4 reactive chlorine ? Hal atoms. Under Suitable conditions, these react gradual ItalSN JNCYial (I) ly with compounds which contain replaceable hydrogen atoms. If different starting materials are used one after wherein Hal is a halogen atom, in particular chlorine, or 25 the other, then compounds of the general Formula II also bromine or fluorine, is reacted with one to four mols are obtained wherein R, R2, R3 and R4 represent differ of ammonia and/or organic compounds which contain at ent organic radicals bound by Sulphur or oxygen atoms least one replaceable hydrogen atom bound to a hetero or a substituted amino group and, in an incomplete reac atom in a homeopolar manner, the reaction being per tion, some of them also represent halogen. In the first formed in the presence of acid binding agents, to form. 30 place, the halogen atoms of the side chain react, and this condensation products of the general formula even in the cold. The compounds thus formed with one or two replaceable halogens are still very reactive bodies which, depending on the organic substituent, still react with the moisture in the air and, therefore, must be stored 35 in closed vessels. In general, reaction products having a secondary amine are more stable than those having a primary amine. Tetrameric cyanogen bromide can be (II) produced in a similar way to tetrameric cyanogen chlo wherein R represents a substituted amino group such as ride and it can be reacted as defined in this invention. a low molecular mono- or di-alkylamino group hav 40 Finally, on reacting tetrameric cyanogen chloride with ing alkyl radicals containing 1-4 carbon atoms such potassium fluoride, starting materials of the Formula as the methyl, ethyl, n-propyl, isopropyl, n-butyl-, iso used according to the invention can be obtained, in which butyl, sec. butyl or tert, butyl radicals, in particular “Hal” completely or partially represents fluorine. a low molecular dialkylamino group, or it represents Relatively simply constructed, uncoloured, aliphatic, an anilino or N-(lower alkyl)-anilino group possibly 45 cycloaliphatic, araliphatic, aromatic or heterocyclic hy substituted in the aromatic nucleus by halogen, in par droxyl compounds, mercaptains, primary and secondary ticular by chlorine, particularly the N-methyl or N amines and also heterocyclic compounds having NH ethyl anilino group, or it represents an organic radi groups as ring members are used as starting materials cal, particularly an aromatic radical bound by an oxy with at least one replaceable hydrogen atom bound in a gen or a sulphur atom, advantageously a possibly hal 50 homeopolar manner by way of a hetero atom. Thus the ogen-substituted phenylmercapto radical, such as, e.g. non-metals of the 5th and 6th group of Mendelejeff's a chlorophenylmercapto radical, periodic system of the elements are used as hetero atoms R2, R3 and R4 independently of each other represent hal promoting the linkage in the condensation products ac ogen such as e.g. chlorine, bromine and fluorine, par cording to the invention, i.e. the elements of the 5th and ticularly chlorine, or they represent substituted amino 55 6th group of the first and second periods. Starting ma radicals corresponding to the definition of R, terials used according to the invention can also contain whereby in the case of a nuclear-substituted anilino or still further replaceable hydrogen atoms, advantageous N-(lower alkyl)-anilino group, an aromatic radical en ly of slighter reactivity, such as, e.g. in amino groups the abling the azo coupling to take place such as, e.g. the 1 reactivity of which is reduced by vicinal substituents. hydroxy-3-sulphonaphthaneaminocarboxy-(6)-radical, or 60 This is the case, for example, in aromatic o-aminoaryl a diazotisable group, such as, e.g. an amino group and, sulphonic acids. Examples of suitable starting materials possibly, other substitutents such as, e.g. the sulpho group, for the production of condensation products according to can be present, and the invention are: methanol, ethanol, propanol, isopro panol, n-butanol, isoamyl alcohol, n-hexyl alcohol, ally wherein R1 and R2 together with the vicinal carbon atom 65 alcohol, methoxyethanol, ethoxyethanol, n-butyloxyeth can also represent a benzimidazoline ring. anol, dimethylaminoethanol, diethylaminoethanol, cyclo Tetrameric cyanogen chloride is utilised principally as hexanol, methylcyclohexanol, benzyl alcohol, p-chlo tetrameric cyanogen halide according to the invention. robenzyl alcohol, c-phenylethyl alcohol, 2-phenyleth It is produced, for example, on polymerising cyanogen anol, 3-phenylpropanol, phenol, o-chlorophenol, p-nitro 8,058,843 3. 4 phenol, 2,4-dichlorophenol, 4-isopropylphenol, 4-tert. ethyl ether, anisol, tetrahydrofurane, dioxan and buta butylphenol, 4-tert, amylphenol, 2,4-diisopropylphenol, none. Reactions with several mols of a low molecular al 1-naphthol, 2-naphthol, furfuryl alcohol, tetrahydrofur cohol can also possibly be performed in an excess thereof. furyl alcohol, acetone glycerine, 2-pyrrolidinyl ethanol In general, the first and also the second halogen atoms and 2-piperidinyl ethanol; methyl mercaptan, ethyl mer of the tetrameric cyanogen halides react much more eas captan, isopropyl mercaptan, allyl mercaptain, thiophe ily at low temperatures, e.g. at room temperature or un nol, p-nitrothiophenol, 2-mercaptobenzoxazole and 2 der, than the third. The third and, particularly the mercaptobenzthiazole; methylamine, ethylamine, n-pro fourth, halogen atom must be reacted at elevated tem pylamine, isopropylamine, n-butylamine, isobutylamine, perature and often even under pressure. Naturally, the n-amylamine, n-hexylamine, allylamine, methallylamine, 10 most expedient reaction conditions also depend on the re 3-methoxypropylamine, 3-isopropoxypropylamine, eth activity of the other reaction components. anolamine, ethylenediamine, N-acetylethylenediamine, Basic reaction components act simultaneously as acid cyclohexylamine, dodecylamine, hexadecylamine, octa binding agents and, therefore, possibly double the molar decylamine, N-dodecylethylenediamine, N-dodecylpro amount must be added; however, also the usual acid bind pylenediamine-(1,2), benzylamine, aniline, o-chloraniline, 5 ing agents such as, e.g. tertiary organic nitrogen bases, m-chloraniline, p-chloraniline, p-bromaniline, o-toluidine, can be used. Acid binding agents are also particularly m-toluidine, p-toluidine, o-nitraniline, m-nitraniline, p advantageous in reactions with alcohols, phenols or mer nitraniline, 2,4-dimethyl aniline, 1-aminobenzene-2-sul captains; possibly these starting materials can be convert phonic acid, 1-aminobenzene-3-sulphonic acid, 1-amino ed into their salts with such agents as, for example, alkali benzene-4-sulphonic acid, 4-nitro-1-aminobenzene-2-sul 20 metals, amides, hydroxides or carbonates, before the reac phonic acid, 1-aminobenzene-2,5-disulphonic acid, 4 tion with the tetrameric cyanogen halides. methyl- 1 -aminobenzene - 2 - Sulphonic acid, 3 - chloro In the reaction of tetrameric cyanogen halide in the 4-aminobenzene-1-sulphonic acid, 5-chloro-2-aminoben first step with components which contain two condensable Zene-1-sulphonic acid, 4-nitro-2-aminobenzene-1-sulphon groups in positions suitable for the formation of rings, ic acid, 2-nitro-4-aminobenzene-1-sulphonic acid, 1,3-di 25 e.g. at neighbouring carbon atoms, also condensation aminobenzene-4-Sulphonic acid, 1,3-diamino-6-methyl products in ring form are obtained. Thus, for example, benzene-4-sulphonic acid, 2-amino-4-acetamidobenzene in the condensation of aromatic o-diamino,
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