SU298115A1 - METHOD OF OBTAINING TRISAMINO-S-TRIAZINE DERIVATIVES - Google Patents

Description

This invention relates to a process for the preparation of new trisamino-5-triazine derivatives having higher waxy properties.

A method is proposed for the preparation of trisamine o-5-triazine derivatives of the general formula

Nyn

wherein)

/ R.

A - NX group

R,

where Ri is C-Cb-alkyl and R2-Ci-C18 alkyl;

/ RI

in - group - N, R.

where Hi and R2 are the above values or the residue of pyrrolidine, piperidine, 4-methylpyralezine, morpholine, hexamethylenimine;

C-residue of pyrrolidium, piperidine, 4-methyl piperazine, morpholi; on or hexamethylenimine or a group of the general formula

NY

//

where B has the above meaning, and X is an alkylimide residue, and is | SINGING in that cyanuric chloride is treated with either 2 moles of one or a mixture of 2 moles of different secondary amines containing residues Ri and R2, and

1 mole of pyrrolidine, piperidine, 4-methylpiperazine, morpholine, or gaxamethyleneimine, or 1 mole of a secondary amine NHRiR2 and

2 mol of pyrrolidine, piperidine, 4-methylpiperazine, morpholine or hexamethylenimine, or 1 mole of a secondary amine NHRiR2,

1 mol of pyrrolidine, piperidine, 4-methylpiperazine, morpholine or hexamethylenimine and 1 mol of a secondary O amine containing the indicated group of the general formula //, or

2 mol of one or a mixture of 2 mol of various secondary amines NHRiR2 and 1 mol of a secondary amine containing a group of the general formula //.

The process is conducted in the presence of a solvent or diluent and a proton acceptor. The product is isolated in a known manner.

Example 1. To a solution of 185 h. cyanuric chloride in 1000 parts of carbon tetrachloride with intensive stirring and temperature from 0 to 5 ° C. add 87.1 parts of morpholine, then add a solution of 54 parts of sodium carbonate in 300 parts of water, stir for 2 hours and add dropwise a solution of 290 parts of N-methyl-N-n-octadecylamine in 1000 parts of water at 10–15 ° C and then a solution of 54 parts of sodium carbonate in 300 parts of water. The reaction mixture is slowly heated and then refluxed for 5 hours. After completion of the reaction, the solvent was distilled off. The residue is mixed with 1500 hours of acetone. The insoluble portion is sucked off, thoroughly washed with water and dried. 2-chloro-4-morpholino-6-N-methyl-N-n-octadecylamino-S-triazine is obtained, which, after recrystallization from alcohol, melts at 52-54 ° C.

482 parts of 2-chloro-4-morpholino-6-N-methyl-N-noctadedylamino-3-triazine and 110 parts of N-methyl piperazine; are dissolved by heating at 4000 parts of xylo 1 a and 45 parts of powder are added. caustic soda The reaction mixture is heated under reflux under nitrogen and; Yood separator. At the end of the water separation, the mixture is heated under reflux es, 3 hours. The hot reaction mixture is filtered, the filtrate is evaporated to dryness in vacuo, and the residue is mixed with 4000 parts of acetone. The solid, undissolved portion is separated, thoroughly washed with water and dried in vacuo. 2-H-methylpiperazino-4 is obtained - morpholino-6-M-methyl-K-n-octadecylamino-5-triazine, "released after non-recrystallization from dioxane, it melts at 46-51 ° C.

Example 2. 37 parts of cyanurhloride pactBO are sprinkled in 400 parts of anhydrous toluene and a solution of 120 parts of TH, H-dimethyl-Nn-octadecylamine in 400 parts of anhydrous toluene is added dropwise at room temperature. Then the reaction mixture is heated in a stream of nitrogen under reflux until the calculated amount of chloromethane is removed. After distilling c. vacuum of solvent gives 2-chloro-4,6-, bis-N-methyl-n-octa "decylamino-5-triazine, m. pl. 58-62 ° C (from acetone).

34 parts of 2-chloro-4, b-bis-N-methyl-N-n-0Ktadecylamino-3-triazine are heated for 5 hours at 110-115 ° C in a stream of nitrogen with 10 parts of morpholine. After cooling, the outbreak morpholine and its hydrochloride are removed, and the residue is dried. 2-morpholino-4,6-bis-.Y-methyl-M-noctad, ecylamino-5-triazine, m.p. 80-82 ° C (from ethyl alcohol).

Example 3. 67.8 parts of 2-chloro-4,6-.bis-M-methyl-Mn-octadecylamino-3-triazine and 68.7 parts of 2-ethylamino - 4,6-bis-M- Methyl Mn-octadecylamino-5-triazine p. is dissolved in 400 parts of anhydrous pyridine by heating and stirring, then heated in a stream of nitrogen for 18 hours with a fridge and the mixture is filtered hot. The filtrate is evaporated in vacuo to dryness, the residue is thoroughly washed with water and dried in vacuo. 6Y-methyl-1CH- "- octadecylamino-5-triazine- (6) yl-ethylamine is obtained, which, after recrystallization from acetone, melts at 55-57 ° C.

Compounds of the general formula / are obtained analogously (see table).

Table

-N

-N

-N

Cifhi

Continued table.

LzS-YS, VNZ7

C, H

O-N-YN)

N

Cjh

/ -L-N-r TrN

-N /

vVNzSS

AL-N VN N-CH3

C:, Nd

/

N

-N N-СНз

CioH21)

/

N

-N 0

С | бНзз СзН7

N

SSCHON

Sd Nts

N.

S.NNZE

 HOH Cj-N-CzH Br

Subject invention

Claims (5)

1. The method of obtaining trisamic-Z-triazine derivatives of general formula VV NyN C / R. in which A is a group - N, R, where Ri is Ci-Cb-alkyl and Rz is Cю-C18 алки alkyl; ./ B - group - Nv R, wherein RI and Rs have the aforementioned meanings or a residue of pyrrolidine, piperidine, 4-methylpiperazine, morpholine or hexamethylenimine; C is a pyrrolidine, piperidine, 4methyl piperaz a, morpholine or hexamethylenimine residue or a group of the formula "VV :;;; where B has the above value, and X is the alkyl-residue ;, Continued table. N - ЯзС - НдСг-К-С бИзз N - H7C3-N-C, 2H2s H9C4-N-C, oH2t HsC Н „С5-Y-С, бНзз .N. SzNg . Well MSS NWOSH S -N- M HoCN.N characterized in that cyanuric chloride is treated with one or a mixture of two different secondary amines having RI and R2 residues and pyrrolidine, piperidine, 4-methyl: piperaziony, morpholine or hexamethyleneimine in the presence of a solvent or diluent and proton acceptor, followed by isolation of the target product by a method of a method . 2. An exemplary claim according to claim 1, characterized in that 1 mole of pyrrolidine, piperidine, 4-am ylpiperazine, morpholine or hexamethyleneimine is taken per 2 moles of one or a mixture of 2 moles of various secondary amines. 3. Method for and. 1, characterized in that 2 moles of pyrrolidine, piperidine, 4-methylpiperazine, morpholine or hexamethyleneimine are taken per mole of the secondary amine. 4. The method according to claim 1, wherein 1 mole of pyrrolidine, piperidine, 4-methylpiperazine, morpholine or hexamethyleneimine and 1 mole of a secondary amine having a group of the general formula VV -AT Nyn 30 1112 5. The method according to claim 1, wherein; what m r on 2 mol of one or a mixture of 2 mol of different-T m secondary amines take 1 mole of secondary amine, having a group of the general form - 5X Step B, X are as defined above. 298115 at