Synthesis of salicylamides with improved reaction kinetics and i

Details Synthesis of salicylamides with improved reaction kinetics and i Synthesis of salicylamides with improved reaction kinetics and i

1984-11-20

1987-10-20

Naff, David M.

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

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

548179, 548163, 548195, 549474, 549480, 549481, 564134, 564139, 564169, 564179, C07C10322

Patent

active

047015276

ABSTRACT:
A method of synthesizing with improved reaction kinetics and improved effective yields salicylamide compounds of the formula: ##STR1## wherein R.sub.1 is a substituent selected from the group consisting of --H, --COC.sub.n H.sub.2n+1 and --C.sub.n H.sub.2n+1 wherein n is an integer with a value of from 1 through to about 15, R.sub.2 is a substituent selected from the group consisting of --H, --CN, --NO.sub.2, --F, --Cl, --Br, --I, --CF.sub.3, --CBr.sub.3, --CCl.sub.3, --CI.sub.3 and R.sub.1 and R.sub.3 is an R.sub.2 substituted heterocyclic compound selected (e.g.) from the group consisting of furan, thiazole, benzothiazole and purine which comprises reacting a phenyl salicylate ester bearing an R.sub.1 substituent on the benzene ring of the salicylic acid portion thereof with an R.sub.2 substituted aniline or a heterocyclic amine NH.sub.2 --R.sub.3 and with a Lowry-Bronsted acid catalyst, optionally in the presence of an inert solvent such as a halogenated or unhalogenated aromatic compound or a polyethylene glycol of average molecular weight 1000 to 6000 or mixtures thereof at a temperature of above about 150.degree. C. for about one half to about 4 hours. When the Lowry-Bronsted acid catalyst takes the form of the hydrochloride salt of the reactant aniline or heterocyclic amine the amount of the free reactant aniline or heterocyclic amine is reduced proportionately.

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