Process for the preparation of alkylhydroxyanilinothiotriazine d

Details Process for the preparation of alkylhydroxyanilinothiotriazine d Process for the preparation of alkylhydroxyanilinothiotriazine d

1991-05-13

1992-02-04

Ford, John M.

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

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

C07D25146

Patent

active

050861735

ABSTRACT:
A process for the preparation of compounds of formula I ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.6 cycloalkyl or phenyl, and R.sub.3 and R.sub.4 are each independently of the other C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.6 cycloalkyl, phenyl, phenyl which is substituted by C.sub.1 -C.sub.6 alkyl and/or hydroxy, or phenyl-C.sub.1 -C.sub.4 alkyl. The process comprises reacting a compound of formula III ##STR2## with a nitrite in aqueous or aqueous/organic medium to a compound of formula II ##STR3## extracting said compound of formula II from the reaction solution with a solvent, hydrogenating said compound, without isolation, in the cited solvent and in the presence of a palladium catalyst, to the corresponding p-aminophenol, and reacting said aminophenol, without isolation, with cyanuric chloride and a compound of formula HSR.sub.3 or HSR.sub.4 or a mixture of compounds of formulae HSR.sub.3 and HSR.sub.4. The products are obtained in high yield and purity.

REFERENCES:
patent: 3156690 (1964-11-01), Dexter et al.
patent: 3240749 (1966-03-01), Dexter et al.
patent: 3255191 (1966-06-01), Dester et al.
patent: 3257354 (1966-06-01), Dexter et al.
Albert J. Am. Chem. Soc. 76, 4985 (1954).
Gilman et al J. Org. Chem. 19, 1067 (1954).

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