Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1997-02-07
2000-10-10
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
544196, 544200, 544204, 544205, 564398, C07D25116, C07D25118, C07D25142, C07D25148
Patent
active
061303321
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a method for alkylation of 1,3,5-triazine derivatives which comprises reacting the 1,3,5-triazines having at least one or more amino groups or mono-substituted amino groups with aldehydes or ketones in the presence of a catalyst of a metal of group VII and/or group VIII in the periodic table and hydrogen-containing gas and alkylating said at least one or more amino groups or mono-substituted amino groups.
The substituted 1,3,5-triazine derivatives obtained by alkylation of the amino group(s) or mono-substituted amino group(s) on the carbon atom(s) of the triazine ring of the 1,3,5-triazine derivatives in the present invention are a group of useful compounds which are widely used as intermediates of fine chemicals such as agricultural chemicals, medications, dyestuffs, paints and the like, as resin materials, among others, as aminoplasts-forming components, and as flame-retardant materials.
TECHNICAL BACKGROUND
As a method for producing substituted triazines, various methods have been known so far. It is reported, for example, a method in which a compound of the formula (III) ##STR1## wherein X.sup.4 and X.sup.5 each represent an diethylamino group and X.sup.6 represents an ethylamino group or X.sup.4 and X.sup.5 represent an amino group and X.sup.6 represents an ethylamino group or diethylamino group is produced by the reaction of 2-chloro-1,3,5-triazine with ethylamine (J. Amer. Chem. Soc., vol. 73, p. 2984, 1951).
It is reported a method in which a compound of the formula (III) wherein X.sup.4, X.sup.5 and X.sup.6 each represent an ethylamino group is produced by the reaction of 2,4,6-trimethylthio-1,3,5-triazine with ethylamine (Chem. Ber., vol. 18, p. 2755, 1885).
It is reported a method in which a compound of the formula (III) wherein X.sup.4 represents an amino group, X.sup.5 represents an amino group or an octylamino group, and X.sup.6 represents an octylamino group is produced by the reaction of 2,4,6-triamino-1,3,5-triazine with octylamine hydrochloride (U.S. Pat. No. 2,228,161, 1941).
It is reported a method in which a compound of the formula(III) wherein X.sup.4 represents a phenyl group, and X.sup.5 and X.sup.6 each represent a butylamino group is produced by the reaction of 2-phenyl-4,6-diamino-1,3,5-triazine with butylamine (U.S. Pat. No. 2,385,766, 1945). Further, 2,4,6-1,3,5-triazine derivatives produced from cyanuric chloride are used as a flame retardant of a thermoplastic polymer (Japanese Patent Application Laid-Open No. Hei 3-1215564). Specific examples of the derivatives described in this Japanese Patent Application Laid-open No. Hei 3-215564 are as follows as a part thereof. ##STR2##
Examples of reaction of aminotriazines with carbonyl compounds such as aldehydes or ketones are represented by the reaction example in which hydroxymethylation was conducted by melamine and an aqueous formalin solution under the weakly alkali condition. (J. Amer. Chem. Soc., vol. 69, p. 599, 1947).
The method described in J. Amer. Chem. Soc., vol. 73, p. 2984, 1954 requires a condensation agent in an amount of more than a stoichiometrical amount in many cases and causes formation of by-products such as salts and the like which is often industrially problematic. The method described in Chem. Ber., vol. 18, p. 2755, 1885 causes formation of by-products such as sulfur compounds and the like which is often industrially problematic. The methods described in U.S. Pat. No. 2,228,161 (1941) and U.S. Pat. No. 2,385,766 (1945) require high temperatures in the reaction. Besides, the former method causes formation of by-product ammonium chloride. Any of the above-mentioned methods conduct the substitution reaction with the leaving group by using substituted amines which are not said to be industrially inexpensive, and this is one of the reasons that substituted triazines cannot be supplied at low costs.
In the reactions of amino trizines with carbonyl compounds such as aldehydes or ketones, the reactivity of amino group in the triazine rings is low. Therefore, as
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Fukue Yasuo
Hashiba Isao
Ishikawa Makoto
Mizusawa Ken-ichi
Tanaka Norio
Balasubramanian V.
Nissan Chemical Industries Ltd.
Shah Mukund J.
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