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Crystals 2011, 1(4), 254-259; doi:10.3390/cryst1040254

Communication

Synthesis and Crystal Structure of 1-(3-Fluorophenyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one

Aamer Saeed ^1,*  and Ulrich Flörke ²

¹ Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan ² Department Chemie, Fakultät fur Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany

* Author to whom correspondence should be addressed.

Received: 22 October 2011 / Accepted: 7 December 2011 / Published: 8 December 2011

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Abstract: The base catalyzed intramolecular nucleophilic cyclization of 1-(2-bromobenzoyl)-3-(2-fluorophenyl)thiourea (1) in the presence of N,N-dimethyl formamide (DMF) afforded the 1-(3-fluorophenyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one (2) by an intramolecular nucleophilic substitution S_NAr mechanism. The structure was supported by the spectroscopic data and unambiguously confirmed by the single crystal X-ray diffraction data. It crystallizes in the orthorhombic space group P na2₁ with unit cell dimensions a = 22.430(4), b = 8.1478(16), c = 13.522(3) Å, V = 2471.2(9) ų. There are two independent molecules per asymmetric unit that are linked to centrosymmetric AB-dimers via intermolecular N-H…S bonds.

Keywords: : quinazolinone; 3-aryl-2-thioxo-2,3-dihydroquinazolin-4(1H)-ones; synthesis

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