The method of obtaining asymmetrically substituted triazines

 

(57) Abstract:

Triazine formula I obtained in a simple way, represent valuable intermediate products for the synthesis of dyes, pharmaceuticals and plant protection products. Asymmetrically substituted triazine General formula I, where R1is hydrogen, methyl or ethyl, R2and R3- C1-8-alkyl, C3-8alkenyl, C3-8-quinil, C3-8-cycloalkyl, phenyl, benzene, or phenethyl, each of which may substituted by fluorine, chlorine, phenyl, C1-4-alkyl or C1-4-alkoxyl, produced by interaction of the guanidine derivative of the formula II with a carboxylic acid derivative of formula IV, R3-COOR4where R4accepts any values specified for R2in the presence of alcohol R2OH, and a base or amide carboxylic acid and in the presence of salt or salevideo compounds of magnesium, calcium, aluminum, zinc, copper, iron, cobalt, Nickel or chromium. The proposed method provides receiving triazines of the formula I from more accessible and having a lower reactivity of the raw materials. This method can be carried out without isolating the product obtained at intermediate stages. 12 C.p. f-crystals.

< / BR>

N IS R>
in which R1is hydrogen, methyl or ethyl;

R2and R3independently from each other - C1-C8-alkyl, C3-C8alkenyl, C3-C8-quinil, C3-C8-cycloalkyl, phenyl, benzyl or phenethyl, each of which may have substituents, such as fluorine, chlorine, phenyl, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxyl.

Asymmetrically substituted triazine can be obtained by various methods, for example, based on N-cyanamide, interaction with complexes of Vilsmeier (see R. L. N. Harries, Aust. J. Chem. 34 (1981) 623) based on esters of N-sanimidget (see Germany application DE-A 3411202; M. A. Perez, J. L. Soto, Heterocycles, 20 (1983) 463; K. R. Huffman and F. C. Schaefer, Journ. Org. Chem. 28 (1963) 1816) or on the basis of biguanidine (see S. L. Shapiro et al., Journ. Org. Chem. 25 (1960) 379; U.S. patent US-A 2535968). Publications known to further interaction guanidinoacetic with dimethylsulfate and derivatives of carboxylic acids (see, for example, H. Eilingsfeld, H. Scheuermann, Chem. Ber. 100 (1967) 1874; application Germany DE-A 1670147; European patent application EP-A 545149), as well as the interaction of trichloroacetaldehyde derivative triperoxonane acid (see Germany application DE-A 4034078). Using all of these methods it is impossible to get nutricomp vermeil-1,3,5-triazines according to the method, known from the publication Jakugaku Zasshi 95, 499-511 (1975), is that N-cyanoguanidine transferred to copper complexes of N-amidino-O-alkalization, derivatives of urea release with hydrogen sulfide and then subjected to the interaction with the ether triperoxonane acid according to the following reaction scheme:

< / BR>
< / BR>
From the patent DDR DD-A-252374 known variant of this method, where instead of chloride of copper (II) apply the copper acetate.

For the implementation of these methods requires stoichiometric amounts of copper salts; in the absence of copper salts instead of N-amidino-O-alkalization is formed mainly ganymedian (see Kyushu Kogyo Daigaku Kenkyu Hokoku, No. 12, 69-78 (1962)).

Interaction hydrochloride N-amidino-O-alkalization with ethylparathion in a mixture of ethanol/NaOC2H5you can get a corresponding chloromethylthiazole only with very low output. The original product you can select from copper complex.

Getting chelate complexes based on languagein using copper acetate or zinc chloride in methanol is described in R. I. Dutta and A. Syamal in Coord. Chem. Rev., volume 2, 1967, pp. 441-457. From the publication in the Chemistry of Heterocyclic Compounds, volume 25, 1989, pages 547-550, Issey acid, deliver triazine.

Similar by zinc sulfate forms a chelate complex, which after treatment with boiling water is decomposed in the second stage to sulfate amidino-O-methylisoleucine (see U.S. patent US-A 3360534, a patent IN India-A 167500) and then in the third stage, it can be subjected to interaction with acetic anhydride (see S. Lotz, G. Kiel, G. Gattow, Zeitschrift anorg. allgem. Chemie 604 (1991), 53-62) or methyl ether triperoxonane acid (see T. Tsujikawa, Jakugaku Zasshi 95, see above), receiving the triazine with the release of 31%, respectively 26%.

These last methods are very expensive multi-stage methods, which when using esters allow you to get the appropriate triazine only with a very low output, and the use of anhydrides require the preparation of stoichiometric amounts of carboxylic acids, the management of which the corresponding anhydrides possible only at very high cost. There is usually a need to highlight unsafe in Toxicological terms, it is difficult filtered complexes of heavy metals, which are then subjected to interaction in an inert solvent with anhydrides, such as were mentioned above, the described methods have one major drawback, namely in their implementation necessarily produces large quantities of salts of heavy metals in the form of organic sludge, the removal of which involves considerable difficulties.

In U.S. patent US-A 4886881 presents one-step synthesis of 2-aminotriazines who receive based on languagein and triethylorthoformate in the presence of acid catalyst (Lewis acid), such as zinc chloride. As solvents, it is recommended to use dimethylformamide and acetonitrile.

In European patent application EP 0482477A describes a method for asymmetrically substituted triazines interaction guanidine derivative, for example, N-substituted derivative of N-triftoratsetofenona with the corresponding derived triperoxonane acid.

The basis of the invention was based on the task to find a way that would make getting triazines of the formula I by the interaction of languageyou with esters of carboxylic acids, more affordable and at the same time having a lower reactivity than the corresponding anhydrides or areafile. This method should be carried out on vozmozhnosti). The problem is solved by a method of obtaining asymmetrically substituted triazines of the General formula I

< / BR>
in which R1, R2and R3have videopreteen values

namely, that languagein formula II

< / BR>
where R1has the specified values,

subjected to interaction with ether carboxylic acids of General formula IV

R3- COOR4< / BR>
where R3has the specified values;

R4may take any of the values specified for R2,

in the presence of an alcohol of General formula III

R2OH,

where R2has the specified values.

The interaction is carried out in the presence of a base or amide carboxylic acid selected from the group comprising N,N-di(C1-C4-alkyl)formamide, N, N-di(C1-C4-alkyl)ndimethylacetamide or N-organic and in the presence of salt or salevideo compounds of magnesium, calcium, aluminum, zinc, copper, iron, cobalt, Nickel or chromium.

Serving as the starting material substituted languagein well known. N-methyl-N, respectively N-ethyl-substituted derivatives can be obtained from languageline and diallylsulfide, as described by A. E. Kratovil and A. S. Bio-additive salt, and in this case released during the reaction a suitable acid neutralizing additives appropriate base, such as methanolate sodium.

Applying the received triazines of the formula I R2can represent, preferably, for example, C1-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl; C3-C4alkenyl as prop-2-EN-1-yl, 1-methylprop-2-EN-1-yl, but-2-EN-1-yl or but-Z-ene-1-yl; C3-C4-quinil, such as prop-2-in-1-yl or but-2-in-1-yl; C3-C6-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; especially preferred of them C1-C4-alkyl, in particular methyl.

The radical R2can carry, in addition, also other inert under the respective reaction conditions substituents, such as, for example, fluorine or chlorine, phenyl, C1-C4-alkyl, C1-C4-halogenated or C1-C4-alkoxy.

Based on the target application triazines of the formula I R3can be a preferably C1-C4-halogenated, especially fluorine or chloromethyl, or fluorine - or chloroethyl, as CCl3, CF3, CF23, CF3and C2F5.

According to the invention the interaction languagein formula II with an alcohol of the formula III (respectively, R4IT is formed by hydrolysis of ester (IV) is carried out in the presence of a base. Unexpected reactivity metallogenetic complexes can increase due to the possibility of reaction with esters of the formula IV, although these esters have a much smaller reaction activity compared with the corresponding carboxylic acid anhydrides or areafile.

For use as bases are suitable as inorganic and organic bases. As inorganic bases is preferred hydroxides of alkali and alkaline earth metals and organic bases, preferably using tertiary amines, such as C1-C4-trialkylamine, for example, triethylamine, pyridine or N-methylmorpholine. It is advisable to use as the basis of an alcoholate of an alkaline or alkaline earth metal transformable alcohol R2OH. This anion can be formed in situ, for example, from the corresponding alkali metal or sodium amide or g is L. equivalent towards languagemenu formula II. Large quantities are also possible, but this usually does not give any additional benefits.

Instead of the base can also be used amide carboxylic acid from the group comprising N,N-di(C1-C4-alkyl)formamide, N,N-di(C1-C4-alkyl)ndimethylacetamide or N-organic. As examples are dimethylformamide, diethylformamide, dimethylacetamide and diethylacetamide. Supplements amides of carboxylic acids have proved themselves especially when using heavy metals, in particular copper, as originators of chelate complexes.

The number of amide carboxylic acid is typically 1-30, primarily 5-10 mol. equivalents relative to languageline formula II. It may be appropriate to use carboxylic acid amide as a solvent.

As salts or calivigny compounds of magnesium, calcium, aluminum, zinc, copper, iron, cobalt, Nickel and chromium can be considered soluble in the reaction medium products, such as halides, for example fluorides, chlorides or bromides, nitrates, sulfates, or if necessary, phosphates, Vendo other metals, regardless of whether it has a good solubility or not, does not play a significant role, as the decisive factor in this choice are material costs. As examples, the following compounds: MgCl2, Mg(OCH3)2, CaCl2, Zn(NO3)2, Cu(CH3COO)2), AlCl3, AlBr3, ZnCl2, ZnBr2, CuCl2, NiBr2, CrCl3, CaO, Ca(NO3)2, Mg(NO3)2, MgO, ZnO, FeCl2, FeCl3, Fe(NO3)2, Fe(NO3)3. Especially preferred of these chlorides, primarily CaCl2and ZnCl2.

One of the benefits of the proposed according to the invention method is that its implementation largely or even completely possible to refuse the presence of heavy metals and for reasons of ecology and toxicology to do more secure in this respect, elements such as magnesium and especially calcium. Accordingly, particularly preferred are the soluble salts of these elements. Very good results were obtained also when using zinc compounds.

Salt, respectively delevigne compounds of the above elements can be used in stechiometric formula II, for example, in molar amounts of from 0.001 to 2.0, especially 0.005 to 1.0 per 1 mol languagein formula II.

When using heavy metals should be minimal and should apply only catalytic amounts, for example, less than 0.6 mol per 1 mol languagein. When using salts of magnesium and calcium, particularly preferably this amount is 0.01 to 1.0, especially 0.05 to 0.5 mol. Naturally, it is also possible amount in excess of stoichiometric with respect to languageline formula II, for example, 1 to 2 mol per 1 mol languagein II, however, economic considerations favor the use of amounts less than stoichiometric.

Starting material of formula III, or may be formed in situ from the ether carboxylic acids of the formula IV (R2identical to R4), or it is added to the reaction mixture (preferably as a solvent). While using III as a solvent, it is recommended to choose an alcohol component, respectively, complex ether of the formula IV (i.e. R2identical to R4to avoid the formation of side products.

The molar ratio between languageyou formula II and the spirit fo the knowledge to apply in the amount of from 0.5 to 10, first of all, from 1 to 5 mol per 1 mol languagein II. As the esters of formula IV among especially preferred should include the following compounds: esters of C1-C4-alkane - or halogenecarbonate acid, for example, C1-C5-alkalemia perfluorinated ethers or perforirovannoi C1-C3-carboxylic acids.

Examples of these esters are the methyl ester acetic acid, ethyl ester acetic acid, methyl ester propionic acid, ethyl ester propionic acid, methyl ester triperoxonane acid, methyl ester DIPEROXY acid, methyl ester forexpros acid, methyl ester of trichloroacetic acid, methyl ester dichloracetic acid, methyl ester Chloroacetic acid, ethyl ester triperoxonane acid methyl and ethyl ester pentafluoropropionic acid methyl and ethyl ester pentafluoropropionic acid. Based on the target application triazines of the formula I as intermediates for crop protection products are the most preferred source compounds of the formula IV is methyl ether triperoxonane acid and ethyl ester triperoxonane acid.

2HE, for example, methanol, is preferably used as solvent. According to one of the preferred embodiments as a basis in these cases, choose the corresponding alcoholate, such as methanolate alkali metal, and the process is carried out in the presence of calcium salts or zinc salts. The process preferably also can be carried out in the presence of N,N-dimethylformamide, and salts of copper.

The reaction temperature is in the range from 0 to 200oC, primarily 20 - 150oC), particularly preferred temperature of the reaction mixture by heating under reflux.

Special reaction conditions concerning pressure is not required, it is carried out mainly at atmospheric pressure or when the pressure corresponding to the reaction medium.

The reaction can be conducted in a continuous mode and discontinuous. In continuous mode, the reagents are preferably injected through a tubular reactor or a cascade of reactors with agitators.

According to one particularly preferred embodiments of the method according to them by: first prepare a mixture of languagein formula II, complex ester of formula IV and salts of alkaline-earth metal or salts of other metals (respectively calivigny compounds) in quantities less than stoichiometric, in alcohol R2HE serves as a solvent, and then enter the additives of the base, for example, an alcoholate of an alkali metal, such as NaOR2or KOR2, after which the mixture is heated under reflux.

As a rule, after the reaction mixture no longer remains languagein, the reaction according to the usual method of finish (for example, using thin-layer chromatography, liquid chromatography, high pressure or gas chromatography).

Further processing in order to obtain the product of formula I of the method is carried out, generally, by using conventional methods such as distillation, filtration, centrifugation, or supplements of water and subsequent extraction.

The crude products can, if necessary, subjected to further purification, for example, by crystallization, distillation or chromatographic methods.

Triazine formula I obtained in a simple way by the method according to the invention, is a valuable intermediate which sannich, for example, in the following publications: European patent application EP-A 508348 and EP-A 111442 or Germany application DE-A 4038430.

Examples of the synthesis of

Example 1. 2-Amino-4-methoxy-6-trifluoromethyl-1,3,5-triazine.

21 g (0.25 mol) of N-languageline, 3.4 g (0,025 mol) of anhydrous zinc chloride and 160 g (1.25 mol) of methyl ether triperoxonane acid load in 400 ml of methanol, heated to 50oC for 10 h type pump 50 g (0,27) 30 mol% solution of sodium methylate. Then the solvent is almost completely removed, the residue was washed with 250 ml water and 250 ml of diluted hydrochloric acid and dried at 60oC/20 mbar. In this way get to 43.2 g (0.22 mol, 89%) of 2-amino-4-methoxy-6-trifluoromethyl-1,3,5-triazine in the form of a colourless powder (ghvd: > 99 wt.%). TPL: 161-163,5oC.

Example 2. 2-Amino-4-methoxy-6-trifluoromethyl-1,3,5-triazine.

56,6 t (0.5 mol) of calcium chloride (98%, powder) and 210 g (2.5 mol) of N-languagein download in 2 l of methanol. With stirring is heated under reflux and stirred while heating for 1 h, after which obtain a homogeneous solution. The mixture is then cooled to room temperature and add 640 g (5.0 mol) of methyl ether triperoxonane acid; Daae white precipitate. After heating for 2 h under reflux the mixture is cooled to room temperature and additives of concentrated hydrochloric acid to establish a pH of about 6. Then the methanol is distilled off, gradually add about 2 liters of water, separating the precipitated fine white crystals and dried under vacuum.

Output: 402,4 g (2,07 mol; 83% of theory).1H-NMR spectrum (270 MHz, CDCl3, TMS (internal standard), (part./million)): 6,45 br (1H); 5,88 br (1H); 4,03 s (3H).

Example 3. 2-Amino-4-methoxy-6-trifluoromethyl-1,3,5-triazine.

84 g (1 mole) languagein and 100 g (0.5 mol) of copper acetate load in 600 ml of methanol and within 7 h heated under reflux. After cooling to 20oC charging mixture is sucked off, and solid copper complex is separated and dried under vacuum. 41,4 g (0.1 mol) of this residue load in 200 ml of methanol for 15 min added dropwise 45 g (0.25 mol) of 30% aqueous solution of sodium methylate. Then added dropwise with 76.8 g (0.6 mol) of methyl ether triperoxonane acid and heated for 2 h under reflux. Mixture is allowed to cool to 40oC, filtered red-purple solid (28.6 g) and concentrate the mother liquor. The remainder Prome-4-methoxy-6-trifluoromethyl-1,3,5-triazine.

41,4 g (0.1 mol) of copper complex of example 3 download in 300 ml of DMF and 20oC for 15 min added dropwise a 51.2 g (0.4 mol) of methyl ether triperoxonane acid. Then heat up first for 1 h to 50oC and continue heating for 5 h to 90oC. the Reaction solution blue color concentrate and the residue is mixed with 100 ml of water and 100 ml of diluted hydrochloric acid. After the extraction of the suspension, washing the filter cake (the cake) and drying of the residue gain of 23.4 g (0.12 mol, 60%) of the above triazine as colourless powder.

Example 5. 2-Amino-4-ethoxy-6-trifluoromethyl-1,3,5-triazine.

of 8.4 g (0.1 mol) languagein and 35.5 g (0.25 mol) of ethyl ether triperoxonane acid load in 46 g of ethanol and within 5 min add the suspension of 8.5 g (0.125 mol) of sodium methylate in 39,8 g of ethanol. After the introduction of additives to 5.66 g (0.05 mol) of calcium chloride the reaction mixture for 7 h heated under reflux. Then at 20oC add 0.5 ml of concentrated hydrochloric acid and remove the ethanol. Next, add 100 g of water and the suspension is sucked off. The residue is washed with 50 ml water and dried at 50oC/20 mbar. In this way gain of 18.6 g (0,089 mol, 89%) of 2-amino-4-ethoxy-6-trifter the er 6 2-Amino-4-deformity-6-methoxy-1,3,5-triazine.

A solution of 1.9 g (23 mmol) of N-languageline and 2.6 g (23 mmol) of calcium chloride in 50 ml of methanol is stirred for 90 minutes under reflux. After cooling the reaction mixture to 20-25oC in her first quickly added dropwise 5.0 g (45 mmol) of methyl ether DIPEROXY acid, and then slowly 4.1 g (23 mmol) of a solution of methanolate sodium (30 wt. % in methanol), and then saliva. After stirring for 2 hours while heating under reflux volatile components are removed in a water jet vacuum at a bath temperature 40oC, the residue is partitioned between 100 ml of water and 100 ml ethyl ester acetic acid, the organic phase is separated and dried over MgSO4. After removal of the solvent at 40oC in a water-jet vacuum get mentioned in the title compound in the form of oil with a small amount of impurities (1.1 g, 6.3 mmol; 28% of theory), which if necessary can crystallize by rubbing with a mixture of simple ether/hexane (volume:volume=1:3).1H-NMR spectrum (400 MHz, CDCl3, TMS (internal standard), (part./million)): 7,44 br (1H); 6,97 br (1H); 6,27 t (2JH-F= 55 Hz, 1H); 3.96 points s (3H). 13C-NMR spectrum (100 MHz, CDCl3/CD3>JC-F25 Hz); 168, 8mm s ( -NH2); 111,3 t ( HF2,1JC-FS Hz); 54,7 s (O H3).

1. The method of obtaining asymmetrically substituted triazines of the General formula I

< / BR>
where R1is hydrogen, methyl or ethyl;

R2and R3independently of each other C1-C8-alkyl, C3-C8alkenyl, C3-C8-quinil, C3-C8-cycloalkyl, phenyl, benzyl or phenethyl, each of which may have substituents, such as fluorine, chlorine, phenyl, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxy,

by reacting guanidine derivative with a derivative of carbonic acid, characterized in that as a derivative of guanidine use languagein General formula II

< / BR>
where R1has the specified values,

and as a carboxylic acid derivative use ether carboxylic acids of General formula IY

R3-COOR4,

where R3- has the specified values;

R4may take any of the values specified for R2,

and interaction is carried out in the presence of an alcohol of General formula III, R2-OH, where R2- has the specified values, and a base or amide carboxylic key is amide or N-organic, and in the presence of salt or salevideo compounds of magnesium, calcium, aluminum, zinc, copper, iron, cobalt, Nickel or chromium.

2. The method according to p. 1, characterized in that the base used alcoholate or a tertiary amine.

3. The method according to p. 1, characterized in that the base used alcoholate of alkali or alkaline earth metal alcohol of General formula III.

4. The method according to p. 1, characterized in that as salts and calivigny compounds used halides, nitrates, sulphates, alcoholate or acetates of the elements referred to in paragraph 1.

5. The method according to p. 1, wherein the salt or delevigne connection on p. 1 is used in a molar amount of 0.001 to 2.0 to 1 mol languagein formula II.

6. The method according to p. 1, wherein the salt or solvenia the heavy metal compounds on p. 1 are used in quantities less than stoichiometric with respect to languageline formula II.

7. The method according to p. 1, characterized in that the use of salt or delevigne compounds of alkaline earth metals such as calcium or magnesium.

8. The method according to p. 7, characterized in that salts of calcium or magnesium are used in a molar amount of 0.01 to 2.0 to 1 mol tianguang C1-C6-alkilany the perfluorinated ether or perforirovannoi C1-C3-carboxylic acids.

10. The method according to p. 1, characterized in that as ether carboxylic acid using methyl ether triperoxonane acid, an alcohol of the formula III - methanol as a base - methanolate alkali metal.

11. The method according to p. 1, characterized in that the methyl ether triperoxonane acid is subjected to interaction with languageline General formula II in the presence of methanolate alkali metal and calcium salts.

12. The method according to p. 1, characterized in that the methyl ether triperoxonane acid is subjected to interaction with languageline General formula II in the presence of N,N-dimethylformamide and copper salts.

13. The method according to p. 1, characterized in that the methyl ether triperoxonane acid is subjected to interaction with languageline General formula II in the presence of methanolate alkali metal and zinc salts.

 

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< / BR>
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