2-Anilino-3-(2-hy­droxy­phen­yl)quinazolin-4(3H)-one–triphenyl­phosphine oxide (1/1)

Hong-Ling Wang; Xiao-Bao Chen; Xu-Hong Yang; Dong-Feng Pan; Jun-Kai Ma

doi:10.1107/S1600536810035324

. 2010 Sep 8;66(Pt 10):o2522. doi: 10.1107/S1600536810035324

2-Anilino-3-(2-hydroxyphenyl)quinazolin-4(3H)-one–triphenylphosphine oxide (1/1)

Hong-Ling Wang ^a,^*, Xiao-Bao Chen ^b, Xu-Hong Yang ^a, Dong-Feng Pan ^c, Jun-Kai Ma ^b

PMCID: PMC2983302 PMID: 21587516

Abstract

In the title compound, C₂₀H₁₅N₃O₂·C₁₈H₁₅OP, the pyrimidinone heterocycle and the fused phenyl ring are inclined at 1.92 (7)°. Only the hydroxy group is involved in hydrogen bonding, whereas the amino group is shielded from potential acceptors.

Related literature

For the synthesis of the title compound, see: Yang et al. (2008 ▶).

Experimental

Crystal data

C₂₀H₁₅N₃O₂·C₁₈H₁₅OP
M _r = 607.62
Monoclinic,
a = 18.9139 (3) Å
b = 10.3201 (2) Å
c = 18.2145 (3) Å
β = 117.771 (1)°
V = 3145.83 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 298 K
0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.980, T _max = 0.987
38085 measured reflections
7826 independent reflections
5767 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.134
S = 1.01
7826 reflections
412 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL .

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035324/bt5345sup1.cif

e-66-o2522-sup1.cif^{(27.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035324/bt5345Isup2.hkl

e-66-o2522-Isup2.hkl^{(382.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3ⁱ	0.815 (18)	1.862 (19)	2.6436 (15)	160.1 (18)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to Hubei Medical University Education Committee (grant No. 2009QJ12) for financial support and acknowledge the Sophisticated Analytical Instrument Facility, Central China Normal University, Wuhan, for the data collection.

supplementary crystallographic information

Comment

Quinazoline-4(3H)-one derivatives have numerous biological properties. We have recently focused on the synthesis of heterocyclic compounds using an aza-Wittig reaction. We present here the crystal structure of the title compound (Fig. 1), which can be used as a precursor for obtaining bioactive molecules.

In the crystal structure, the pyrimidinone heterocycle and the adjacent benzene ring are not coplanar, but inclined at 1.92 (7) °. Only the hydroxyl group is involved in hydrogen bonding, whereas the amino group is shielded from potential acceptors.

Experimental

To a solution of iminophosphorane (1.40 g, 3.0 mmol) in anhydrous THF (10 ml) was added isocyanatobenzene (3 mmol) under nitrogen at room temperature. After reaction, the mixture was allowed to stand for 10 h at 273–278 K, the solvent was removed under reduced pressure and diethyl ether/petroleum ether (1:2 v/v, 20 ml) was added to precipitate triphenylphosphine oxide. After filtration, the solvent was removed to give 1-phenyl- 3-(2-ethoxycarbonylphenyl) carbodiimide, which was used directly without further purification. To a solution of 1-phenyl- 3-(2-ethoxycarbonylphenyl) carbodiimide in THF (15 ml) was added 2-aminophenol (3 mmol). After the reaction mixture was allowed to stand for 0.5 h, the solvent was removed and anhydrous ethanol (10 ml) with several drops of EtONa in EtOH was added. The mixture was stirred for 2 h at room temperature. The solution was concentrated under reduced pressure and the residue was recrystallized from ethanol to give the title compound (yield 79%).