Ethyl 1-(2-hy­droxy­eth­yl)-2-propyl-1H-benzimidazole-5-carboxyl­ate

Nurasyikin Hamzah; Nurziana Ngah; Shafida Abd Hamid; Aisyah Saad Abdul Rahim

doi:10.1107/S1600536811037421

. 2011 Sep 30;67(Pt 10):o2704. doi: 10.1107/S1600536811037421

Ethyl 1-(2-hydroxyethyl)-2-propyl-1H-benzimidazole-5-carboxylate

Nurasyikin Hamzah ^a,^b, Nurziana Ngah ^a, Shafida Abd Hamid ^a,^*, Aisyah Saad Abdul Rahim ^b

PMCID: PMC3201285 PMID: 22058794

Abstract

In the title compound, C₁₅H₂₀N₂O₃, the benzimidazole ring is essentially planar, with a maximum deviation from the mean plane of 0.012 (1) Å. The crystal structure is stabilized by intermolecular O—H⋯N hydrogen bonds, forming centrosymmetric dimers, which are connected in the [100] direction through weak C—H⋯O contacts.

Related literature

For the synthesis of the title compound, see: Arumugam et al. (2010 ▶); Kappe (2004 ▶). For general background and therapeutic properties of benzimidazole derivatives, see: Rao et al. (2002 ▶); Khalafi-Nezhad et al. (2005 ▶); Tonelli et al. (2010 ▶); Chen et al. (2007 ▶). For the low-temperature device used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₅H₂₀N₂O₃
M _r = 276.33
Triclinic,
a = 8.5081 (3) Å
b = 8.5573 (3) Å
c = 10.0117 (4) Å
α = 94.671 (3)°
β = 106.903 (2)°
γ = 98.334 (3)°
V = 684.16 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.60 × 0.20 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.946, T _max = 0.994
10526 measured reflections
2401 independent reflections
2075 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.087
S = 1.08
2401 reflections
187 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037421/bh2376sup1.cif

e-67-o2704-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037421/bh2376Isup2.hkl

e-67-o2704-Isup2.hkl^{(118KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811037421/bh2376Isup3.cml

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
O3—H3A⋯N2ⁱ	0.86 (3)	1.98 (2)	2.8047 (17)	159.6 (17)
C11—H11A⋯O2ⁱⁱ	0.99	2.48	3.2901 (19)	139

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

NH, SAH and ASAR gratefully acknowledge the International Islamic University Malaysia (IIUM) for FRGS Grant (FRGS0510–119), MOSTI (304/PFARMASI/650544/I121) and MOSTI (CLB10–01) for funding the synthetic chemistry work.

supplementary crystallographic information

Comment

Benzimidazole compounds possess diverse functions in biological activities such as anti-HIV (Rao et al., 2002), antibacterial (Khalafi-Nezhad et al., 2005), antiviral (Tonelli et al., 2010) and antifungal (Chen et al., 2007). On the other hand, the use of microwave irradiation to assist the chemical process helps to reduce the reaction time, producing better yields and cleaner reactions (Kappe, 2004). In continuation of our study on benzimidazole derivatives (Arumugam et al., 2010), we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzimidazole ring [C1···C6/N1/C7/N2] is essentially planar with maximum deviation of 0.012 (1) Å for atom C4. The bond lengths and angles are in normal ranges and are in agreement with those of ethyl 1-sec-butyl-2-phenyl-1H- benzimidazole-5-carboxylate (Arumugam et al., 2010). In the crystal structure, the molecule is stabilized by O3—H3A···N2 intermolecular hydrogen bond (symmetry code as in Table 1) to form dimers, which are further connected via weak C—H···O contacts to give chains in the [100] direction (Fig. 2).

Experimental

A mixture of ethyl 3-amino-4-[(2-hydroxyethyl)-amino]benzoate (0.10 g, 0.22 mmol), K10-montmorillonite (0.26 g), butyraldehyde (0.07 g, 0.95 mmol) and 1 ml of MeCN were irradiated in CEM^TM microwave at 80 °C, 150 W, 5 bar and hold for 5 minutes. Then, another aliquot of aldehyde was added and the reaction was irradiated again at the same conditions as before. The progress of the reaction was monitored by TLC (Hex:EtOAc, 1:4). After completion, the mixture was filtered, washed with DCM and evaporated in vacuo. The resulting crude mixture was chromatographed with PLC (Hex:EtOAc,1:4). The desired compound was recrystallized with hot EtOAc which was slowly evaporated to give colorless single crystals.