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HHHHHHHHHRH USOO5086172A United States Patent (19) 11 Patent Number: 5,086,172 Beck 45 Date of Patent: Feb

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HHHHHHHHHRH USOO5086172A United States Patent (19) 11 Patent Number: 5,086,172 Beck 45 Date of Patent: Feb HHHHHHHHHRH USOO5086172A United States Patent (19) 11 Patent Number: 5,086,172 Beck 45 Date of Patent: Feb. 4, 1992 (54) PREPARATION OF Primary Examiner-John M. Ford 2,4,6-TRICYANO-1,3,5-TRIAZINE Attorney, Agent, or Firm-Sprung Horn Kramer & (75) Inventor: Gunther Beck, Leverkusen, Fed. Woods Rep. of Germany (57) ABSTRACT (73) Assignee: Bayer Aktiengesellschaft, A process for the preparation of 2,4,6-tricyano-1,3,5- Leverkusen, Fed. Rep. of Germany triazine, comprising reacting a 2,4,6-trihalogeno-1,3,5- (21) Appl. No.: 637,386 triazine of the formula 22 Filed: Jan. 3, 1991 Hai (30) Foreign Application Priority Data Jan. 10, 1990 (DE) Fed. Rep. of Germany ....... 4000480 51) Int. Cl............................................. CO7D 251/24 Hall - els Hall (52) U.S. Cl. .................................................... 544/180 58) Field of Search ......................................... 544/180 in which (56) References Cited Hall and Hal independently of one another represent chlorine or fluorine, with an alkali metal cyanide or PUBLICATIONS an alkaline earth metal cyanide. Carrington et al., Chemical Abstracts, vol. 64, entry 195e (1966). 7 Claims, No Drawings 5,086,172 1. 2 products, which are prominent owing to the high reac PREPARATION OF tivity of the tricyanotriazine, is so largely suppressed 2,4,6-TRICYANO-1,3,5-TRIAZINE that the desired tricyanotriazine is still obtained in good yields. The invention relates to a new process for the prepa- 5 The invention therefore relates in particular to a pro ration of 2,4,6-tricyano-1,3,5-triazine (cyanuric cya cess for the preparation of 2,4,6-tricyano-1,3,5-triazine, nide). which is characterized in that 2,4,6-trihalogeno-1,3,5- 2,4,6-Tricyano-1,3,5-triazine is an interesting chemi triazines of the formula (I) are reacted in aliphatic or cal compound; for example, it forms electrically-con cyclic ethers or aliphatic nitriles under mild reaction ducting charge transfer complexes with tetrathiafulva 10 conditions with not more than a small excess over the lene (see Synthetic Metals 19, page 415 (1987)). In addi stoichiometrically required amount of alkali metal cya tion, the compound reacts on treating with methanol nides or alkaline earth metal cyanides. under certain conditions with the formation of 2-cyano Of the aliphatic and cyclic ethers and aliphatic nitriles 4,6-dimethoxy-1,3,5-triazine (Chem. Ber. 52, 659 to be used as specific solvents according to the inven (1919)), which, for its part, is a useful intermediate for 5 tion, diethylene glycol dimethyl ether (diglyme), 1,2- the production of highly effective herbicides (see EP-A dimethoxyethane, tetrahydrofuran, propionitrile and 0,094,260). acetonitrile have proved particularly suitable. Acetoni However, until now there has still been no process trile is particularly preferably used. available by which 2,4,6-tricyano-1,3,5-triazine can be Alkali metal cyanides and alkaline earth metal cya prepared in relatively large amounts. The only process 20 nides which are preferably used are the inexpensive described until now for the preparation of the com alkali metal cyanides sodium cyanide and potassium pound consists in heating 2,4,6-triscarboxamido-1,3,5- cyanide. triazine with phosphorus pentoxide and sand (see Tetra In order to replace the three halogen atoms in the hedron (1963) 19, pages 161 to 167, in particular page cyanuric halides of the formula (I), 1.5 moles of alkaline 162 and page 166). 25 earth metal cyanide or 3 moles of alkali metal cyanide However, the2,4,6-triscarboxamido-l,3,5-triazine re are necessary per mole of trihalogeno-triazine. quired as a starting compound must in turn be prepared According to the invention, not more than a small from diethyl oxalate in a complicated four-step process. excess of at most 20 mole-% relative to the molar The yields of pure 2,4,6-tricyano-1,3,5-triazine based on amount theoretically required for the complete reaction the triscarboxamidotriazine are only between 12 to 17% 30 of theory, i.e. the process is not suitable for preparation of the halogen atoms is used. However, it has been of relatively large amounts of the desired tricyanotria found that it can be highly advantageous to work with e. a subequivalent amount of cyanides; a part of the It has now been found that the desired 2,4,6-tricyano trihalogenotriazine corresponding to the subequivalent 1,3,5-triazine can be obtained in a simple manner start amount then in fact remains unreacted; however, as ing from inexpensive starting materials by reaction of tricyanotriazine can be separated in a simple manner alkali metal cyanides or alkaline earth metal cyanides from, for example, unreacted trifluorotriazine and this with 2,4,6-trihalogeno-1,3,5-triazines of the formula recovered trihalogenotriazine can be used again in the next batch, and through the use of a subequivalent amount of cyanide the secondary product formation is Hal (i) 40 reduced, it can be highly efficient to use substantially less than the amount of cyanide stoichiometrically re quired in the process according to the invention. Very generally, 0.3 to 3.6 equivalents of alkali metal cyanide Hall - els Hall or alkaline earth metal cyanide are employed per mole 45 of trihalogenotriazine in the process according to the in which invention. Hall and Hal independently of one another represent The reaction, according to the invention, of the chlorine or fluorine. trihalogenotriazines of the formula (I) with the alkali The invention therefore relates to a process for the preparation of 2,4,6-tricyano-1,3,5-triazine, which is 50 metal cyanides or alkaline earth metal cyanides actually characterized in that 2,4,6-trihalogeno-1,3,5-triazines of proceeds, as can be determined with gas chromato the formula (I) are reacted with alkali metal cyanides or graphic monitoring of the reaction, via the monocyano alkaline earth metal cyanides. dihalogeno and dicyano-monohalogeno-1,3,5-triazine It has been found that 2,4,6-tricyano-1,3,5-triazine is intermediates; in spite of this, essentially only the 2,4,6- obtained in good yields and high purity from 2,4,6-55 tricyano-1,3,5-triazine is formed even on using a trihalogeno-triazines of the formula.(I), preferably from subequivalent amount of cyanide if the reaction is car 2,4,6-trichloro-1,3,5-triazine (cyanuric chloride) or ried out to its completion. 2,4,6-trifluoro-1,3,5-triazine (cyanuric fluoride) in a The reaction, according to the invention, of the simple one-step reaction if the trihalogenotriazines of trihalogenotriazines with the alkali metal cyanides and the formula (I) are reacted with alkali metal cyanides or 60 alkaline earth metal cyanides can be described by the alkaline earth metal cyanides in certain solvents and following reaction equation: under mild reaction conditions and alkali metal cya nides and alkaline earth metal cyanides are used in not Hall more than a small excess over the amount stoichiometri 1. cally required for the reaction. By means of the parame N N NaCN G ters "mild reaction conditions' and "not more than a 1. el small excess of alkali metal cyanides or alkaline earth Hal N Hall metal cyanides", the formation of undesired secondary (I) 5,086,172 3 4. can be removed by recrystallization from benzene or by -continued chromatography. Hall CN EXAMPLES Example 1 N 1. N -Ge. N 1 SN -G 152 g (3.1 mol) of sodium cyanide are added with stirring and with exclusion of moisture to a solution, - N ases -S N ases cooled in an ice bath to 0 to 5 C., of 184.4 g (1 mol) of (III) (IV) cyanuric chloride in 2,500 ml of anhydrous acetonitrile. 10 The reaction mixture is vigorously stirred for about 70 CN hours, initially with ice bath cooling for about 12 hours 1s and then at room temperature. N N The reaction mixture is worked up with the exclusion of atmospheric moisture as follows: The residue is fil - Nes 15 tered off and concentrated to dryness in vacuo in a (II) rotary evaporator at room temperature. The oily resi due is stirred vigorously with anhydrous dichlorometh Monocyanodihalogeno-1,3,5-triazine (III) and ane (about 1 l) at room temperature. After filtering off dicyanomonohalogeno-1,3,5-triazine (IV) can above all undissolved material, the filtrate is concentrated to dry be isolated and detected by gas chromatography if the 20 ness in a rotary evaporator, first at room temperature, reaction according to the invention is carried out with a then at 30° C. The residual crude 2,4,6-tricyano-1,3,5- subequivalent amount of cyanides and prematurely dis triazine (109 g=70% of theory) in the form of a dry, continued. The retention times of (III) and (IV) are crystalline brownish powder is obtained in the form of between the retention times of (I) and (II) in the gas 25 pure white crystals by sublimation at 100 to 110 C./0.1 chromatogram. mbar. The reaction according to the invention is carried out Yield: 92.7 g (=59.4% of theory). under mild conditions, i.e. at temperatures of -50 to IR (KBr) in cm-l; 2276, 2255, 1653, 1555, 1515, 1339, --80 C., preferably at -40 to +50° C. and particu 939, 822. larly preferably at -30 to +30 C. The temperature 30 The positions of the absorption bands essentially depends on the trihalogeno-triazine used; the extremely agree with the data in the literature (measured in Nujol; reactive cyanuric fluoride requires lower reaction tem Tetrahedron 19, 161-167 (1973).
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