Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1998-06-22
2000-10-03
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
544197, C07D25142, C07D25148, C07D25154
Patent
active
061275387
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
In a first aspect, the present invention relates to a method of modifying 1,3,5-triazine derivatives characterized by reacting a 1,3,5-triazine derivative having at least one amino or mono-substituted amino group on a carbon atom or atoms on its ring with an alcohol in the presence of a metal catalyst and hydrogen to introduce an alkyl or alkenyl group into the at least one amino or mono-substituted amino group. And, in a second aspect, the present invention relates to a method of modifying 1,3,5-triazine derivatives as described in claim 1, characterized by reacting a 1,3,5-triazine derivative having at least one amino or mono-substituted amino group on a carbon atom or atoms on its ring with a dihydric alcohol in the presence of a metal catalyst and hydrogen to introduce an alkyl group having a hydroxyl group into the at least one amino or mono-substituted amino group.
The substituted 1,3,5-triazine derivatives obtained by the modification of the amino group or groups attached to the triazine ring carbon or carbons are useful compounds which are used widely as intermediates for various fine chemicals such as agricultural chemicals, medicines, dyes, paints, and the like, as various resin materials, in particular as a component for aminoplast molded materials and also as flame retarding materials.
BACKGROUND ART
As for the synthetic method for substituted triazine derivatives, various synthetic methods have heretofore been known. For example, it has been reported a synthetic method for those compounds of the formula (III) ##STR1## wherein X.sup.4 and X.sup.5 represent each a diethylamino group, and X.sup.6 represents an ethylamino group, or X.sup.4 and X.sup.5 represent each an amino group, and X.sup.6 represents an ethylamino group or a diethylamino group, which method includes the reaction of 2-chloro-1,3,5-triazine derivative with ethylamine (J. Amer. Chem. Soc., vol. 73, p.2984 (1951)). Those compounds of the formula (III) wherein X.sup.4, X.sup.5 and X.sup.6 represent each an ethylamino group have been reported by a synthetic method which includes reacting 2,4,6-trimethylthio-1,3,5-triazine with ethylamine (Chem. Ber., vol. 18, p.2755 (1885)). Those compounds 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 have been reported by a synthetic method which includes reacting 2,4,6-triamino-1,3,5-triazine with octylamine hydrochloride (U.S. Pat. No. 2,228,161 (1941)).
Those compounds of the formula (III) wherein X.sup.4 represents a phenyl group and X.sup.5 and X.sup.6 represent each a butylamino group have been reported by a synthetic method which includes reacting 2-phenyl-4,6-diamino-1,3,5-triazine with butylamine (U.S. Pat. No. 2,385,766 (1945)).
Particularly, in recent years, development of compounds introduced with a substituent having a hydroxyl group is becoming increasingly active. For example, there is a description of a compound of the formula (VI) ##STR2## having carcinostatic activity (U.S. Pat. No. 5,534,625 (1996)).
Further, it has been reported that compounds of the formula (VII) ##STR3## are useful as an aminoplast modifier (U.S. Pat. No. 4,668,785. (1987)).
Heretofore, various synthetic methods have been studied for synthesizing these compounds. For example, for the compounds of the formula (VI), there is a report of addition reaction between an N-substituted triazine derivative and formalin (U.S. Pat. No. 5,534,625 (1996).
Furthermore, for the N-substituted triazine derivatives of the formula (VII) having hydroxyethyl groups as a substituent, there is a report of transamination reaction between melamine and ethanolamine (U.S. Pat. No. 4,668,785 (1987)). Similarly, transamination reaction between melamine and isopropanolamine is also reported (U.S. Pat. No. 4,618,676 (1986)).
Also, development has been under way of synthetic methods which catalytically produce various new N-substituted triazine derivatives, such as a method for preparing N-substituted tri
REFERENCES:
patent: 2228161 (1941-01-01), Zerweck et al.
patent: 2385766 (1945-09-01), Thurston
patent: 4618676 (1986-10-01), Ebel et al.
patent: 4668785 (1987-05-01), Ebel et al.
patent: 5534625 (1996-07-01), Jarman et al.
patent: 5792867 (1998-08-01), Tanaka et al.
Hudlicky, Milos., Reductions in Organic Chemistry, 4-8, 10-12,40,49, 62-63,66-69, 1984.
Paquette L.A., Encyclopedia of Reagents for Organic Synthesis 1257-1258, 3785,4401-4402, 1995.
Fieser and Fieser, Reagents for Organic Synthesis, vol. 1, p. 140, 1965.
Hofmann, A.W., "Einwirkung des Ammoniaks und der Amine auf den Sulfocyanursauremethylather und das Cyanurchlorid. Normale alkylirte Melamine.," Chem. Ber., vol. 18, pp. 2755-2800 (1885).
Kaiser, Donald W. et al., "Cyanuric Chloride Derivatives. II. Substituted Melamines," J. Amer. Chem. Soc., vol. 73, pp. 2984-2986 (1951).
Lubczak, Jacek, ".sup.1 H-NMR Study of Reaction of Melamine with Oxiranes," Journal of Applied Polymer Science, vol. 58, 559-564 (1995).
Smolin, Edwin M. et al., "s-Triazines and Derivatives," The Chemistry of Heterocyclic Compounds, Interscience Publishers, Inc., 1959, pp. I-XXIV, 1, 216-269, 308-389.
Fukue Yasuo
Ishikawa Makoto
Mizusawa Ken-ichi
Tanaka Norio
Balasubramanian V
Nissan Chemical Industries Ltd.
Shah Mukund J.
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