Patent GB-1142546-A (GB)
Title: New, substituted, biologically-active s-triazines and the preparation thereof
IPC: C07D251/52
Filed: 1967-07-13
Abstract: 1,142,546. 1,3,5 - Triazine derivatives. DEUTSCHE GOLD-UND SILBER - SCHEIDEANSTALT. 13 July, 1967 [19 July, 1966; 22 Dec., 1966], No. 32295/67. Heading C2C. Novel 1,3,5-triazine derivatives of the general formula wherein X is a cycloalkyldiimino radical attached to the 5-triazine through a nitrogen atom, optionally having an alkyl or alkylol group with 1-6 carbon atoms attached to the other nitrogen atom; R<SP>1</SP> is a group of the formula -CC1 3 , -OAlk, -SAlk or -NR<SP>3</SP>R<SP>4</SP> in which R<SP>3</SP> and R<SP>4</SP>, which may be the same or different, each represents a hydrogen atom or a linear or branched alkyl group with 1-6 carbon atoms and Alk is an alkyl group with 1-6 carbon atoms; R<SP>2</SP> is a group of the formula -NR<SP>4</SP>NR<SP>5</SP>R<SP>6</SP>,  - NR<SP>4</SP>N=R<SP>7</SP> ,  -NR<SP>8</SP>R<SP>9</SP> or in which R<SP>5</SP> and R<SP>6</SP> have the same meanings as R<SP>3</SP> and R<SP>4</SP> or may represent an aryl radical; R<SP>7</SP> is a linear or branched alkylidene, cycloalkylidene or aralkylidene radical; and R<SP>8</SP> and R<SP>9</SP> have the same meanings as R<SP>3</SP> and R<SP>4</SP> or may represent as morpholinoalkyl, piperazinylalkyl, homopiperazinylalkyl or hydroxyalkyl group or R<SP>2</SP> is a morpholino, piperidino, pyrrolidino or piperazino radical or a linear or branched alkylene diamino radical with 1-6 carbon atoms, the second amino group of which may optionally be substituted by an alkyl or phenyl radical; and acid addition and quaternary ammonium salts thereof are prepared by the following methods: (a) reaction of a 2,4-bistrichloromethyl-s-triazine of the general formula with hydrazine, phenylhydrazine, aminomorpholine, morpholine, piperazine, piperidine or pyrrolidine in the presence of an alkali metal alcoholate to form an s-triazine derivative of the general formula wherein R<SP>4</SP> is a hydrogen atom and one of R<SP>5</SP> and R<SP>6</SP> is a hydrogen atom and the other is the same or a phenyl radical, wherein A is an aminomorpholino, morpholino, piperazino, piperidino or pyrrolidino radical, and optional reaction of the resulting s-triazine derivative of the third general formula above (if R<SP>4</SP>, R<SP>5</SP> and R<SP>6</SP> are all hydrogen atoms) with a ketone or an aldehyde to form an s-triazine derivative of the general formula wherein R<SP>4</SP> is a hydrogen atom; (b) reaction of a 2,4 - bis - trichloromethyl - s - triazine of the second general formula above with an excess of an amine of the general formula HR<SP>3</SP>N-Alk<SP>1</SP>-Y or HR<SP>3</SP>NR<SP>4</SP> in which Y is a morpholino, hydroxy or -NR<SP>3</SP>R<SP>4</SP> group, Alk<SP>1</SP> is a linear or branched alkylene radical with 1-6 carbon atoms and R<SP>3</SP> and R<SP>4</SP> are as defined above or an alkylol radical, in the presence of an alcohol, an organic solvent and an alkali metal hydroxide, or an organic solvent and an alkali metal alcoholate; (c) reaction of a 2-halo-s-triazine of the general formula wherein Hal is a halogen atom, B is a -OAlk, -SAlk or -NR<SP>10</SP>R<SP>11</SP> group and Z is a morpholino, piperidino, pyrrolidino, piperazino or -NR<SP>10</SP>R<SP>11</SP> radical, in which R<SP>10</SP> and R<SP>11</SP> are the same or different and each represents a hydrogen atom or a linear or branched alkyl or hydroxyalkyl group with 1 to 6 carbon atoms, with a cycloalkyldiimine of the formula XH in the presence of an acid-binding agent; (d) reaction of a tris-halogeno-s-triazine with an amine of the seventh general formula above, treatment of the resulting product with an alcohol and at least an equimolar quantity of an acid acceptor and introduction of the resulting 2 - alkoxy - 4 - halo - 6 - amino - s - triazine into an alcoholic solution of the cyoloalkyldiimine of the formula XH to form an s-triazine derivative of the general formula (e) reaction of a tris-trichloromethyl-s-triazine with a cycloalkylidiimine of the formula XH and treatment of the resulting 2,4-bis-trichloromethyl-6-X-s-triazine with an amine of the seventh general formula above to form an s-triazine derivative of the general formula and (f) treatment of a 2,4-bis-halogeno-6- amino-s-triazine of the general formula wherein R<SP>3</SP> and R<SP>4</SP> are defined in regard to the seventh general formula above, with a solution of an acid acceptor in an alkyl mercaptan, the resulting solution being introduced into an alcoholic solution of a cycloalkylidiimine of the formula XH to form an s-triazine derivative of the general formula followed optionally in each case by conversion of the product to an acid addition or quaternary ammonium salt thereof. 2,6 - Trichloromethyl - 4 - homopiperazino - s - triazine is prepared by reaction of tris-trichloromethyl-s-triazine with homopiperazine acetate.