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(12) Patent Application Publication (10) Pub. No.: US 2002/0123628A1 Saijo Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2002/0123628A1 Saijo Et Al US 2002O123628A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2002/0123628A1 Saijo et al. (43) Pub. Date: Sep. 5, 2002 (54) PROCESSES FOR PREPARING TRIAZINE (30) Foreign Application Priority Data COMPOUNDS AND QUATERNARY AMMONIUM SALTS Jul. 10, 2000 (JP)...................................... 2OOO-2O78O2 Publication Classification (76) Inventors: Masako Saijo, Tokuyama-shi (JP); 7 Naoki Hirano, Tokuyama-shi (JP) 8. s - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - coni's (57) ABSTRACT Correspondence Address: Russell D. Orkin In the process of the invention to prepare 4,6-dialkoxy-1,3, 700 Koppers Building 5-triazine-2-halide by reacting a cyanuric halide with an 436 Seventh Avenue alcohol compound Such as methanol in the presence of an Pittsburgh, PA 15219-1818 (US) alkali Such as Sodium hydrogencarbonate, the water content present in the reaction System at the beginning of the reaction is controlled to not more than 0.5 mol based on 1 (21) Appl. No.: 10/070,592 mol of the cyanuric halide or the water content present in the reaction System during the period of the reaction is con (22) PCT Fed: Jun. 29, 2001 trolled to not more than 2.5 mol based on 1 mol of the cyanuric halide. According to the invention, 4,6-dialkoxy (86) PCT No.: PCT/JP01/05650 1,3,5-triazine-2-halide can be prepared in a high yield. US 2002/0123628A1 Sep. 5, 2002 PROCESSES FOR PREPARING TRAZINE COMPOUNDS AND QUATERNARY AMMONIUM SALTS (I) RO TECHNICAL FIELD 0001. The present invention relates to a process for Ry preparing a triazine compound in a high yield, Said triazine compound being useful as an intermediate of pharmaceuti cals or agricultural chemicals, and a process for preparing a )- quaternary ammonium Salt using the triazine compound obtained by the above process, Said quaternary ammonium Salt being useful as a condensation agent. 0007 wherein 0008) R' is an alkyl group of 1 to 4 carbon atoms or BACKGROUND ART an aryl group of 6 to 8 carbon atoms, and X is a 0002. A quaternary ammonium salt wherein a nitrogen halogen atom, atom at the 4-position of morpholine Such as 4- (4,6- 0009 said process comprising reacting a cyanuric dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlo halide with an alcohol compound represented by the ride is quaternized and to the nitrogen atom are bonded a 4,6-dialkoxy-1,3,5-triazin-2-yl group and an alkyl group is a following formula: useful compound as a condensation agent for preparing an ROH ester compound or an amide compound. 0010) wherein 0003. The quaternary ammonium salt can be prepared by 0.011) R' is an alkyl group of 1 to 4 carbon atoms or reacting 2-halo-4,6-dialkoxy-1,3,5-triazine with 4-alkylmor an aryl group of 6 to 8 carbon atoms, pholine, and as a proceSS for preparing the triazine com 0012 in the presence of an alkali to prepare the pound, there is known a process comprising allowing an triazine compound represented by the above formula alcohol compound to act on cyanuric chloride in the pres ence of 3 mol of sodium hydrogencarbonate and 2.7 mol of (I), water based on 1 mol of the cyanuric chloride (SYN 0013 wherein the water content present in the reac THETIC COMMUNICATIONS, Vol. 26, No. 18, pp. 3491 tion System at the beginning of the reaction is not 3494, 1996). more than 0.5 molbased on 1 mol of cyanuric halide. 0014) Another embodiment of the present invention is a PROBLEM TO BE SOLVED BY THE process for preparing the triazine compound, comprising INVENTION reacting a cyanuric halide with the alcohol compound in the 0004. In the above process, however, the yield of the presence of an alkali to prepare the triazine compound, triazine compound is as low as 65% and is not Satisfactory. wherein the water content present in the reaction System Therefore, it is an object of the present invention to provide during the period of the reaction is not more than 2.5 mol a process for preparing the triazine compound in a high yield based on 1 mol of cyanuric halide. and besides to provide a proceSS for efficiently preparing the 0015. In the present invention, a hydrogencarbonate is quaternary ammonium Salt. particularly preferably used as the alkali. MEANS TO SOLVE THE PROBLEM 0016. According to the process of the invention for 0005 The present inventors have earnestly studied in preparing a triazine compound, the desired product can be order to Solve the problem, and as a result, they have obtained in a high yield. happened to find that the yield of the triazine compound is 0017. The other invention is a process for preparing a remarkably increased when the water content present in the quaternary ammonium Salt represented by the following reaction System at the beginning of the reaction or the water formula (III): content present in the reaction System during the period of the reaction is greatly decreased by the use of a hydrogen carbonate in the form of an organic Solvent Suspension or the (III) like, though in the conventional process to react an alcohol RO compound with cyanuric chloride, the hydrogencarbonate is used in the form of an aqueous Solution and hence a large ) v / \ amount of water is present in the reaction System. As a result of further studies, the present inventors have found that N ) ( ) when the water content at the beginning of the reaction is controlled to not more than a specific value, the desired product can be obtained in a high yield even if water formed by the reaction as a by-product is not removed. Based on the 0.018 wherein finding, the present invention has been accomplished. 0.019 R' is an alkyl group of 1 to 4 carbon atoms or 0006 That is to say, the present invention is a process for an aryl group of 6 to 8 carbon atoms, R is an alkyl preparing a triazine compound (2-halo-4,6-dialkoxy-1,3,5- group of 1 to 4 carbon atoms, and X is a halogen triazine) represented by the following formula (I): atom, US 2002/0123628A1 Sep. 5, 2002 0020 said process comprising extracting a triazine alcohol compound as the reaction Solvent, too Small amount compound represented by the above formula (I) from of the alcohol causes aggregation or Solidification to bring the reaction Solution containing the triazine com about troubles in Stirring or the like, and hence, it is pound using a slightly water-Soluble organic Solvent preferable to use the alcohol compound in an amount of 5 to and then mixing the resulting slightly water-Soluble 50 mol, particularly 5 to 30 mol, based on 1 mol of the organic Solution of the triazine compound with a cyanuric halide. morpholine compound represented by the following 0029. The alkali employable in the invention is, for formula (II) to perform reaction; example, a basic Salt Such as a hydrogencarbonate, an organic amine or an inorganic amine, and a hydrogencar bonate is particularly preferably employed. AS the hydro (II) gencarbonate, conventionally known compounds are employed without any restriction. Examples of the hydro gencarbonates employable in the invention include Sodium hydrogencarbonate, potassium hydrogencarbonate and ammonium hydrogencarbonate. Of these, Sodium hydrogen 0021) wherein R is an alkyl group of 1 to 4 carbon carbonate and potassium hydrogencarbonate are preferably atOmS. employed. 0022. According to the above process, production effi 0030) If the amount of the alkali is too small, hydrogen ciency of the triazine compound is high, and hence, from the chloride formed by the reaction of the alcohol compound Viewpoint of the total production process Starting from the with the cyanuric halide is not neutralized, and thereby the primary materials Such as an alcohol compound and a progreSS of the reaction becomes difficult. If the amount cyanuric halide, the quaternary ammonium Salt that is the thereof is too large, the slurry Viscosity becomes high to final desired product can be prepared efficiently. cause troubles in Stirring or the like. Hence, the amount of the alkali is desirably selected from the range of 2 to 3 mol, BEST MODE FOR CARRYING OUT THE preferably 2.05 to 2.8 mol, based on 1 mol of the cyanuric INVENTION halide. 0023 The process for preparing a triazine compound 0031. In the process for preparing a triazine compound according to the invention is not particularly different from according to the invention, an inert organic Solvent is also the conventional process comprising reacting a cyanuric employable in addition to the alcohol compound. Examples halide with an alcohol compound in the presence of an of the organic Solvents employable in the invention include alkali, except that the amount of water present in the reaction aromatic hydrocarbons, Such as benzene, toluene and System at the beginning of the reaction is controlled to not Xylene, aliphatic hydrocarbons, Such as hexane and heptane; more than a Specific value or the amount of water present in halogenated aliphatic hydrocarbons, Such as dichlo the reaction System during the period of the reaction is romethane and carbon tetrachloride, esters, Such as ethyl controlled to not more than a specific value. acetate, propyl acetate and butyl acetate; ethers, Such as 0024. That is to say, as the cyanuric halide, convention diethyl ether, diisopropyl ether, 1,4-dioxane and tetrahydro ally known compounds are employable without any restric furan; nitrites, Such as acetonitrile and propionitrile; amides, tion, and examples thereof include cyanuric chloride, cya such as N,N-dimethylformamide, N,N-dimethylacetamide nuric bromide and cyanuric iodide.
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