Collect. Czech. Chem. Commun.
1981, 46, 246-255
https://doi.org/10.1135/cccc19810246
Reactions of N-benzoyl isothiocyanate with anthranilic acid and methyl anthranilate
Jaromír Kaválek, Milan Kotyk, Said El Bahaie and Vojeslav Štěrba
Organic Chemistry Department, Institute of Chemical Technology, 532 10 Pardubice
Abstract
N-Benzoyl-N'-(2-carboxy- and 2-methoxycarbonylphenyl)thioureas have been obtained by the reaction of N-benzoyl isothiocyanate with anthranilic acid and methyl anthranilate, respectively. Kinetics of cyclization of these compounds into 2-mercapto-3,4-dihydro-4-quinazolone have been studied in water and in methanol. In the base-catalyzed cyclization of N-benzoyl-N'-(2-carboxyphenyl)thiourea the proper cyclization is preceded by solvolysis of the benzoyl group. In the case of N-benzoyl-N'-(2-methoxycarbonylphenyl)thiourea the reaction rate is limited by the base-catalyzed cyclization of the starting benzoyl derivative; the benzoyl group is split off in a subsequent rapid step.
