N-(3,4-Diethoxy­phen­yl)acetamide

Pei-Hua Ma; Kai-Zhi Zhou; Mei-Lian Sun; Xiu-Mei Zhao; Xin Xiao

doi:10.1107/S1600536809018042

. 2009 May 20;65(Pt 6):o1314. doi: 10.1107/S1600536809018042

N-(3,4-Diethoxyphenyl)acetamide

Pei-Hua Ma ^a, Kai-Zhi Zhou ^a, Mei-Lian Sun ^a, Xiu-Mei Zhao ^a, Xin Xiao ^a,^*

PMCID: PMC2969794 PMID: 21583171

Abstract

In the title compound, C₁₂H₁₇NO₃, the conformations of the N—H and C=O bonds are anti to each other. In the crystal structure, N—H⋯O hydrogen-bond interactions help to establish the packing.

Related literature

For the use of acetamides in the synthesis of biologically active compounds, see: Koike et al. (1999 ▶). The benzanilide core is present in compounds with a wide range of biological activity and benzanilides and benzamides are also used extensively in organic synthesis (Saeed et al., 2008 ▶). Various N-substituted benzamides exhibit potent antiemetic activity, see: Vega-Noverola et al. (1989 ▶).

Experimental

Crystal data

C₁₂H₁₇NO₃
M _r = 223.27
Monoclinic,
a = 15.563 (8) Å
b = 8.661 (6) Å
c = 9.305 (7) Å
β = 101.773 (14)°
V = 1227.8 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.24 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.971, T _max = 0.975
6295 measured reflections
2155 independent reflections
1570 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.119
S = 1.08
2155 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018042/at2786sup1.cif

e-65-o1314-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018042/at2786Isup2.hkl

e-65-o1314-Isup2.hkl^{(103.8KB, 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
N1—H1⋯O3ⁱ	0.86	2.08	2.915 (2)	164

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors gratefully acknowledge the Natural Science Foundation of China (No. 20767001), the International Collaborative Project of Guizhou Province andthe Governor Foundation of Guizhou Province for financial support.

supplementary crystallographic information

Comment

Acetamide is an important class of medical intermidate. Many biologically active compounds are synthesized by using acetamide (Koike et al., 1999). The benzanilide core is present in compounds with a wide range of biological activity and benzanilides and benzamides are also used extensively in organic synthesis (Saeed et al., 2008). Various N-substituted benzamides exhibit potent antiemetic activity (Vega-Noverola et al., 1989). The crystal structure determination of the title compound (I) has been carried out in order to elucidate the molecular conformation.

The molecule of the title compound, (Fig. 1), consists of a phenylacetamide group and two ethoxyl groups. The conformations of the N—H and C=O bonds are anti to each other. The C10—C9—O2—C4 and C8—C7—O1—C3 torsion angles are -173.61 (15)° and 178.46 (15)°, respectively. The title compound forms intermolecular H bonds whereas the N1 act as hydrogen-bond donor and the O3 act as hydrogen-bond acceptor, the distance of the N1—H1···O3 hydrogen bond is 2.915 (2) Å (Table 1). In the crystal structure, N—H···O hydrogen bonds interactions may help to establish the packing.

Experimental

Ferrous powder (2.20 g, 0.039 mol), water (15 ml) and acetic acid (3 ml) were reflux for 4 h, the reaction mixture was cooled to room temperature. Then a solution of 1,2-diethoxy-4-nitrobenzene (2.10 g, 0.01 mol) in acetic acid (50 ml) was added to the mixture, the solution was reflux for 6 h. the mixture was filtered, and the resulting solution was added to water (150 ml), much white precipitate was appeared, the mixture was filtered again, the solid product was dissolved in 80 ml ethanol. and then set aside for five days to obtain colourless crystals [yield: 53%].