J Chem Crystallogr (2009) 39:28–31
DOI 10.1007/s10870-008-9424-9
ORIGINAL PAPER
The Synthesis and Crystal Structure of New Bis(3-chlorophenyl)-
[5-methyl-1-(4-methylphenyl)-1,2,3-triazol-4-yl]-methanol
Heng-Shan Dong Æ Guo-Yong Huo
Received: 4 September 2006 / Accepted: 4 June 2008 / Published online: 19 June 2008
Ó Springer Science+Business Media, LLC 2008
Abstract The title compound bis(3-chlorophenyl)-[5-
methyl-1-(4-methylphenyl)-1,2,3-triazol-4-yl]-methanol 8
has been synthesized and established by H NMR, IR and
MS spectra and X-ray diffraction crystallography. Com-
pound 8, C23H29Cl2N3O, Mr = 424.31, crystallizes in the
monoclinic space group P21/c with unit cell parameters
The route of syntheses of the title compound is in
Scheme 1.
Experimental Section
˚
˚
˚
a = 14.5402(6) A, b = 12.5888(5) A, c = 11.6510(5) A, a =
All melting points were uncorrected and determined on an
XT4-100x microscopic melting point apparatus. IR spectra
were obtained in KBr discs on a Nicolet NEXUS 670 FT-IR
spectrometer. MS were performed on a HP-5988A spec-
trometer (EI at 70 eV). 1H NMR spectroscopy (CDCl3) was
recorded on Varian Mercury plus-300 instrument with TMS
as an internal standard.
3
˚
908, b = 100.1838(2), c = 908, V = 2099.05(15) A , Dx =
1.343 mg m-3 and Z = 4. The final R was 0.0514. The
molecular conformation and packing is stabilized by
interactions of intermolecular O1–H1ꢀꢀꢀN30.
Keywords Crystal structure ꢀ Synthesis ꢀ
1H-1,2,3-triazole ꢀ H-bond ꢀ Methanol
Preparation of the Title Compound
Introduction
5-Methyl-1-(4-methylphenyl)-1,2,3-triazol-4-carboxylic
acid 3 was prepared following methods in the literature [8]
Mp182–183 °C(Lit. Mp182–183 °C).
5-Methyl-1-(4-methylphenyl)-1,2,3-triazol-4-carboxylic
acid ethyl ester 4 was prepared following methods in the
literature [8] Mp130–132 °C(Lit. Mp130–132 °C).
1-Bromo-3-chlorobenzene 6 was prepared following
methods in the literature [9].
In recent years in various publications, certain compounds
that 1-aryl-5-methyl-4-substituted-1,2,3-triazoles often
exhibit broad spectrum biological actions [1, 2], antibac-
terial [3], antifungal [4], antiviral [5], anti-inflammatory
and analgetic properties [6]. Some of 1,2,3-triazole deriv-
atives had been reported to inhibit tumor proliferation,
invasion and metastasis [7]. Therefore, it is worthwhile to
investigate these properties of 1,2,3-triazole. As a great
deal of interest has been focused on it, we synthesized a
new title compound.
3-Chlorophenylmagnesium bromide 7 was prepared
following methods in the literature [10].
Preparation of bis(3-chlorophenyl)-[5-methyl-1-(4-methyl-
phenyl)-1,2,3-triazol-4-yl]-methanol
method in the literature [10].
8
was following
A mixture of 3-chlorophenylmagnesium bromide 7
(4.31 g, 0.02 mol) and 35.0 mL ether was dripped to a
mixture of 5-methyl-1-(4-methylphenyl)-1,2,3-triazol-
4-carboxylic acid ethyl ester 4 (0.5 g, 0.002 mol) and
benzene 20.0 mL under stirring. After 3-chlorophenyl-
H.-S. Dong (&) ꢀ G.-Y. Huo
State Key Laboratory of Applied Organic Chemistry, Institute of
Organic Chemistry, College of Chemistry and Chemical
Engineering, Lanzhou University, Lanzhou, Gansu 730000,
People’s Republic of China
e-mail: donghengshan@lzu.edu.cn
123
Dong, Heng-Shan
