2-(2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl­oxy)-N-(o-tol­yl)acetamide

Wen-Sheng Li; Xian-Fu Luo; Yu Wang; Ai-Xi Hu

doi:10.1107/S1600536810018672

. 2010 May 26;66(Pt 6):o1460. doi: 10.1107/S1600536810018672

2-(2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yloxy)-N-(o-tolyl)acetamide

Wen-Sheng Li ^a, Xian-Fu Luo ^a, Yu Wang ^b, Ai-Xi Hu ^a,^*

PMCID: PMC2979639 PMID: 21579528

Abstract

In the title compound, C₁₉H₂₁NO₃, the dihedral angle between the mean planes of the two benzene rings is 38.13 (12)°. The furan ring adopts an envelope-like conformation with the C atom bonded to the dimethyl groups displaced by 0.356 (2) Å from the plane through the other four atoms. In the crystal, molecules are linked into inversion dimers by weak C—H⋯O intermolecular interactions.

Related literature

The title compound is a derivative of Carbofuran, a popular carbamate insecticide, see: Tomlin (1994 ▶). For related structures, see: Xu et al. (2005 ▶); Li et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₉H₂₁NO₃
M _r = 311.37
Monoclinic,
a = 9.0868 (18) Å
b = 8.9708 (18) Å
c = 20.230 (4) Å
β = 92.18 (3)°
V = 1647.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.32 × 0.28 × 0.21 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.985, T _max = 0.991
8246 measured reflections
2961 independent reflections
1649 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.130
S = 1.00
2961 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810018672/jj2028sup1.cif

e-66-o1460-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018672/jj2028Isup2.hkl

e-66-o1460-Isup2.hkl^{(145.3KB, 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
C12—H12A⋯O3ⁱ	0.97	2.60	3.561 (3)	174

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Symmetry code: (i) Inline graphic .

Acknowledgments

We would like to thank the National High Technology Research and Development Program of China (No. 2006 A A03Z460) for financial suppport.

supplementary crystallographic information

Comment

The title compound, (I), C₁₉H₂₁NO₃, is a derivative of the commercial compound Carbofuran (Tomlin, 1994), which is a popular carbamate insecticide. The dihedral angle between the mean planes of the two aromatic rings is 38.13 (12)° (Fig. 1). The five-membered furan ring adopts an envelope-like conformation. All bond lengths (Allen et al. 1987) and angles are within normal ranges. The atom C1 deviates from the C1—C7/O1 plane with a distance of 0.356 (2) Å. Molecules are linked into dimers by weak C—H···O intermolecular interactions which helps stabilize crystal packing(Fig 2).

Experimental

0.10 mol of 2,2-dimethy-2,3-dihydrobenzofuran-7-ol , 0.12 mol chloroacetic acid, 0.25 mol sodium hydrate and 70 ml distilled water were stirred and heated under reflux for 3 h. The reaction mixture was then cooled to 283.15 K and 15 ml concentrated hydrochloric acid was added to give 2-(2,2-dimethyl-2,3-dihydrobenzofuran-7-yloxy)acetic acid as an amber solid of 21.91 g, yield 98.5%. Subsequently, 0.10 mol of dry 2-(2,2-dimethyl-2,3-dihydrobenzofuran-7-yloxy)acetic acid, 0.25 mol thionyl chloride and 80 ml anhydrous was stirred and heated at 353.15 K for 6h. The excess thionyl chloride was then removed under reduced pressure. The residue was cooled to 273.15 K, after which 0.10 mol o-toluidine and 0.20 mol triethylamine was added dropwise. After stirring for an additional 3 h, the reaction mixture was washed with water (3× 40 ml), and the excess toluene removed in vacuo. The residue was purified by recrystallization from a saturated ethanol solution, giving the title compound as a colourless crystalline solid. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of nine days. The identity of the title compound was confirmed by NMR and LC—MS spectroscopy.