Process for the substitution of chlorine atoms of cyanuric chlor

Details Process for the substitution of chlorine atoms of cyanuric chlor Process for the substitution of chlorine atoms of cyanuric chlor

1976-02-10

1977-11-15

Ford, John M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

544204, C07D25150

Patent

active

040586626

ABSTRACT:
There is provided a process, preferably continuous and in a given case successive, substitution of one or two chlorine atoms of cyanuric chloride by one or two amines, which may be the same or different, in the presence of an acid acceptor and in the presence of an organic solvent, particularly for the production of 2-alkylamino-4,6-dichloro and preferably for the production of 2,4-di(alkylamino)-6-chloro-s-triazines wherein there is added 1.00 to 1.05 mole, preferably 1.00 to 1.03 mole of a first amine to a 4.5 to 50 weight % suspension or solution of cyanuric chloride in a mixture of 65 to 85 weight % of xylene, toluene, ethylbenzene, benzene and/or an aliphatic or cycloaliphatic hydrocarbon with 5 to 10 carbon atoms (toluene being preferred) and 35 to 15 weight % of a ketone with 3 to 8 carbon atoms, preferably acetone, while maintaining the temperature between about 0 and about 20.degree. C, preferably about 10 to 18.degree. C., continuously so regulating the pH value of the reaction mixture obtained in accordance with the reaction time by addition of alkali and in a given case, water so that this corresponds to a point within the area bounded by lines ABCD of FIG. 1, which runs through the area beginning with the reaction time t,(step 1)= 0 until reaching a position in the area bounded by the lines BCEF and after reaching a pH of 7.0, preferably 7.2 maintains a temperature of about 10.degree. to about 60.degree. C., preferably about 25.degree. to 40.degree. C., after addition of 0.96 to 1.05, preferably 0.98 to 1.02 equivalents of alkali per mole of cyanuric chloride, adding at least an equimolar amount, preferably 1.00 to 1.02 mole of the second amine per mole of cyanuric chloride and continuously so adjusting the pH value of the reaction mixture obtained depending on the reaction time by addition of alkali that this corresponds to a point within the area which is defined by lines GHIJ in FIG. 3 which passes through the band beginning with the reaction time t(step 2)= 0 of the second reaction step until reaching a position in the area bounded by the lines HIKL and thereby maintaining a temperature of 40 to 70.degree. C., preferably 45.degree. to 55.degree. C. and thereafter working up the product in known manner wherein t.sub.1 is a time of 4 to 10 hours, preferably about 7 hours and t.sub.2 is a time of 2 to 8 hours, preferably about 6 hours and wherein the B C corresponds to the equation, pH = -(12.6/t.sub.1)+ 14.35 and the line H I corresponds to the equation pH = -(24,857/t.sub.2)+ 23.9285. There are also disclosed novel, purified mono and bis alkylamino-cyanoalkylalkylamino -- s -- triazines.

REFERENCES:
patent: 3244712 (1966-04-01), Knusli et al.
patent: 3505325 (1970-04-01), Schwarze et al.
patent: 3590040 (1971-06-01), Ferguson et al.
patent: 3766182 (1973-10-01), Kuhne et al.
patent: 3821220 (1974-06-01), Daugherty et al.
patent: 3947374 (1976-03-01), Lottelman et al.

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