Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1996-02-05
1998-08-11
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
C07D25154
Patent
active
057928673
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP94/01190 filed on Jul. 20, 1994.
TECHNICAL FIELD
The present invention relates to a method for alkylation of 1,3,5-triazine derivatives having at least one or more amino groups or mono-substituted amino groups, which comprises reacting the 1,3,5-triazines having at least one or more amino groups or mono-substituted amino groups with alcohols in the presence of a catalyst of a metal of group VII and/or group VIII in the periodic table.
The substituted 1,3,5-triazine derivatives obtained by alkylation of the 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. Reported are, for example, a method in which a compound of formula (III) ##STR1## wherein X.sup.4 and X.sup.5 each represent an amino group, and X.sup.6 represents an ethylamino group or a 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), a method in which a compound of 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), a method in which a compound of 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), and a method in which a compound of 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, substituted 2,4,6,-triamino-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 3-215564). 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##
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. Nos. 2,228,161 (1941) and 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.
The present inventors have assiduously conducted investigations to solve the problems associated with the prior art, and have consequently found a novel method of alkylating 1,3,5-triazine derivatives in which alkyl group can be introduced into amino group or mono-substituted amino group on carbon atom of the 1,3,5-triazine ring using alcohols which are industrially inexpensive and only water is formed as a by-product. This finding has led to the completion of the present invention.
Further, since the substituted 1,3,5-triazine derivatives obtained by the method of the present invention notably inhibit the inter-m
REFERENCES:
patent: 2228161 (1941-01-01), Zerweck et al.
patent: 2385766 (1945-09-01), Thurston
patent: 4101520 (1978-07-01), Boldizar
patent: 4293692 (1981-10-01), Pai et al.
patent: 4722806 (1988-02-01), Lai et al.
patent: 5155271 (1992-10-01), Aeschlimann
"S-Triazines and Derivatives" The Chemistry of Heterocyclic Compounds, Edwin M. Smolin et al., Interscience Publishers Inc., New York, NY, (1959) pp. 338-388.
Berichte the Deutschen Chemischen Gesellschaft, vol. 18, p. 2755 (1885).
Donald W. Kaiser et al., "Cyanuric Chloride Derivatives. II. Substituted Melamines," J. Amer. Chem. Soc., vol. 73, p. 2984, Jul., 1951.
Fukue Yasuo
Hashiba Isao
Hatanaka Masataka
Ishikawa Makoto
Tanaka Norio
Nissan Chemical Industries Ltd.
Rao Deepak R.
Shah Mukund J.
LandOfFree
Method of alkylating of triazine derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Method of alkylating of triazine derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method of alkylating of triazine derivatives will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-390139