Study of Cyclization of 1-Benzoyl-3-methyl-3-(2-methoxycarbonylphenyl)thiourea to 1-Methyl-2-thioxo-4-quinazolone

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Title:Study of Cyclization of 1-Benzoyl-3-methyl-3-(2-methoxycarbonylphenyl)thiourea to 1-Methyl-2-thioxo-4-quinazolone
Creators:
Kaválek, Jaromír
Macháček, Vladimír
Sedlák, Miloš
Štěrba, Vojeslav
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 58, 5, pp. 1122-1132

Abstract

The reaction mechanism of the title reaction was proposed on the bases of the kinetic study. The reaction takes place in two stages considerably differing in rates. In the first, faster stage, the anion of initial substance cyclizes to 1-methyl-3-benzoyl-2-thioxo-4-quinazolone. The reaction is reversible, the concentration of 1-methyl-3-benzoyl-2-thioxo-4-quinazolone decreases with increasing concentration of methanolate. In the second stage, the benzoyl group rearrangement in the given substance from nitrogen to sulfur and subsequent methanolysis to 1-methyl-2-thioxo-4-quinazolone take place. The rate-determining step is the methanolysis for [CH<sub>3</sub>O<sup>(-)</sup>] &lt; 4 . 10<sup>-3</sup> mol l<sup>-1</sup> and the benzoyl group rearrangement for higher methanolate concentrations.

Title:Study of Cyclization of 1-Benzoyl-3-methyl-3-(2-methoxycarbonylphenyl)thiourea to 1-Methyl-2-thioxo-4-quinazolone
Creators:
Kaválek, Jaromír
Macháček, Vladimír
Sedlák, Miloš
Štěrba, Vojeslav
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:58
Number:5
Page Range:pp. 1122-1132
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19931122UNSPECIFIED
ID Code:229
Item Type:Article
Deposited On:06 Feb 2009 16:59
Last Modified:06 Feb 2009 15:59

Citation

Kaválek, Jaromír; Macháček, Vladimír; Sedlák, Miloš; Štěrba, Vojeslav (1993) Study of Cyclization of 1-Benzoyl-3-methyl-3-(2-methoxycarbonylphenyl)thiourea to 1-Methyl-2-thioxo-4-quinazolone. Collection of Czechoslovak Chemical Communications, 58 (5). pp. 1122-1132. ISSN 0010-0765

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