Solventless process for preparing a tri-substituted triazine

Details Solventless process for preparing a tri-substituted triazine Solventless process for preparing a tri-substituted triazine

C - Chemistry, Metallurgy

07

D

260/249.2

C07D 401/14 (2006.01) C07D 251/70 (2006.01) C07D 403/14 (2006.01)

Patent

CA 2018379

1890051 SOLVENTLESS PROCESS FOR PREPARING A TRI-SUBSTITUTED TRIAZINE ABSTRACT OF THE DISCLOSURE A process is taught for recovering a white reaction product of a cyanuric halide with an amine reactant (white being indicative of the product's high purity), in high yield. In the absence of a solvent for either reactant, the first step comprises reacting the cyanuric halide, as a finely divided solid, with a liquid amine which is to provide a saturated heterocyclic amine group, such as a polysubstituted piperazinone, piperazine, or piperidine as the substitutent for each of the three halogen atoms of the cyanuric halide used. This solventless process carried out under essentially anhydrous conditions, with a large molar excess of the amine reactant chosen, not only short- ens the long time required to make the desired tri-substi- tution in a conventional solvent process, but also obviat- es using a pressurized reactor. Since (i) the reaction temperature is relatively low, (ii) there is no solvent, and (iii) the amine reactants are relatively high-boiling, and the reaction occurs in the liquid phase, there is no build-up of pressure. Fortuitously, the appropriate amount of alkanol and concentrated aqueous alkali provides a partition coefficient such that salt formed by neutraliza- tion of the excess amine hydrohalide is effectively pre- cipitated nearly quantiatively. In addition to providing "easy" processing conditions, the solventless reaction in our process provides higher yields than can be obtained, under comparable conditions, with the 'solvent process'; a lower by-product 'make' because of the low temperature and substantially atmospheric pressure used; and, the batch reaction is completed in less than 12 hr.

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