2,2-Dichloro-1-(2-phenyl-1,3-oxazolidin-3-yl)ethanone

Fei Ye; Ying Fu; Shuang Zhao

doi:10.1107/S1600536810002461

. 2010 Jan 27;66(Pt 2):o445. doi: 10.1107/S1600536810002461

2,2-Dichloro-1-(2-phenyl-1,3-oxazolidin-3-yl)ethanone

Fei Ye ^a, Ying Fu ^a,^*, Shuang Zhao ^a

PMCID: PMC2979863 PMID: 21579860

Abstract

In the title molecule, C₁₁H₁₁Cl₂NO₂, the oxazolidine ring is in an envelope conformation with the O atom forming the flap; the other four essentially planar ring atoms (r.m.s. deviation = 0.012 Å) form a dihedral angle of 91.1 (3)° with the phenyl ring. In the crystal structure, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds, forming one-dimensional chains.

Related literature

For general background to substituted oxazolidines see: Agami et al. (2004 ▶); Guirado et al. (2003 ▶); Tararov et al. (2003 ▶). For the bioactivity of related compounds, see: Hatzios et al. (2004 ▶); Daniele et al. (2007 ▶). For details of the synthesis, see: Fu et al. (2009 ▶).

Experimental

Crystal data

C₁₁H₁₁Cl₂NO₂
M _r = 260.11
Orthorhombic,
a = 19.1775 (13) Å
b = 10.6165 (7) Å
c = 11.3723 (8) Å
V = 2315.4 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.54 mm⁻¹
T = 298 K
0.46 × 0.38 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.780, T _max = 0.897
16860 measured reflections
2846 independent reflections
2323 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.110
S = 1.04
2846 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S1600536810002461/lh2978sup1.cif

e-66-0o445-sup1.cif^{(15KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002461/lh2978Isup2.hkl

e-66-0o445-Isup2.hkl^{(139.8KB, 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
C11—H11⋯O2ⁱ	0.98	2.40	3.312 (2)	156

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thanks the Heilongjiang Province Foundation for Young Scholar (QC2009C44), the China Postdoctoral Science Foundation (20080430951), the Heilongjiang Province Postdoctoral Science Foundation (LBH-Z07012) and the Northeast Agricultural University Doctoral Foundation for generously supporting this study.

supplementary crystallographic information

Comment

Substituted oxazolidines are important synthetic targets due to their biological activity (Agami et al., 2004), pharmacological activity and their extensive use as chiral auxiliaries for the synthesis of many chiral compounds (Guirado et al., 2003; Tararov et al. 2003). Dichloroacetemide compounds have been shown to act as herbicide safeners (Hatzios, 2004; Daniele et al., 2007). As part of our ongoing investigations of oxazolidine derivatives we prepared the title compound and its crystal structure is reported herein.

The molecular structure of the title compound is shown in Fig.1. In the crystal structure, molecules are linked by weak intermolecular C—H···O hydrogen bonds to form one-dimensional chains (Fig. 2).

Experimental

The title compound was prepared by a slightly modified literature procedure (Fu et al., 2009).

Ethanolamine (4.1 g, 0.067 mol) and 7.1g (0.067mol) of benzaldehyde were mixed with 25mL of benzene. The reaction mixture was stirred for 1h at 306-308K. Then, the mixture was heated to reflux and water was evaporated, followed by cooling to 273K and 7.5 mL of 33% sodium hydroxide solution was added. 11.8 g (0.08mol) of dichloroacetyl chloride was added dropwise with stirring, keeping the temperature at 273-277K. Stirring was continued for 1.5h. The mixture was rinsed with water until the pH=7. The organic phase was dried over anhydrous magnesium sulfate and the benzene was removed under vacuum. The crude product was recrystallized with ethyl acetate and light petroleum, white crystals wre obtained. The yield was 58.2%. m.p. 374-377K.

The single-crystal suitable for X-ray structural analysis was obtained by slow evaporation of a solution of the title compound in petroleum ether and ethyl acetate at room temperature.