J Chem Crystallogr (2011) 41:115–120
DOI 10.1007/s10870-010-9847-y
ORIGINAL PAPER
Synthesis and Crystal Structure of 2-Amino-4-(4-hydroxyphenyl)-
5-propylthiazole Ethanol Solvate 0.25 Hydrate
•
Li-Min He Ai-Xi Hu Gao Cao Jiao Ye
•
•
Received: 21 April 2009 / Accepted: 28 June 2010 / Published online: 11 July 2010
Ó Springer Science+Business Media, LLC 2010
Abstract 2-Amino-4-(4-hydroxyphenyl)-5-propylthiazole
was synthesized by the reaction of a-bromo-1-(4-hydroxy-
phenyl)-1-pentone with thiourea. The crystal structure of
its ethanol solvate 0.25 hydrate, C12H14N2OSÁÁÁC2H5OHÁÁ
Á0.25ÁH2O, was determined by X-ray diffraction analysis.
The crystal belongs to monoclinic system, space group C2/c
and insecticidal activity [1]. A series of 5-(2-substituted-
1,3-thiazol-5-yl)-2-hydroxy benzamides and their 2-alkoxy
derivatives were synthesized and screened for their anti-
fungal activities [2]. The 2,4-disubstituted thiazoles were
prepared as anti-bacterial and anti-inflammatory agents [3],
and a series of 4-phenyl thiazole derivatives were synthe-
sized and tested their inhibitory effects on the interleukin-6
secretion stimulated by PTH in osteoblastic cells [4]. In
this paper, the synthesis and characterization of 2-amino-4-
(4-hydroxyphenyl)-5-propylthiazole (1) were reported.
The chemistry to prepare compound (1) is depicted in
Scheme 1.
˚
with a = 20.9046(10), b = 10. 1057(5), c = 30.0017(15) A, b =
3
˚
105.5850(10)°, Z = 8, Mr = 569.77, V = 6105.0(5) A , Dc =
1.240 g/cm3, l = 0.214 mm-1, F(000) = 2440, the final
R = 0.0598 and wR = 0.1825 for 5,911 observed reflections
[I[2r(I)]. Compound (1) is composed by two non-coplanar
ring systems of phenol and thiazole. The structure displays
extensive O–HÁÁÁN, N–HÁÁÁO and O–HÁÁÁO intermolecular
hydrogen bonds.
Experimental
Keywords Crystal structure Á Synthesis Á
2-Amino-4-(4-hydroxyphenyl)-5-propylthiazole
Melting points were measured on an RY-1 melting point
apparatus and uncorrected. 1H NMR spectra were recorded
on a Varian Inova-400 with TMS as internal standard at
400 MHz with chemical shifts (d) expressed in ppm. The
IR spectra were obtained in a KBr disk using an AVA-
TAR360FT spectrophotometer. The mass spectra were
measured on a HP6890-5973.
Introduction
The compounds containing thiazole ring are found to
exhibit biological activities such as antiviral, antifungal
Synthesis of Compound (1)
L.-M. He Á A.-X. Hu (&) Á G. Cao Á J. Ye
College of Chemistry and Chemical Engineering, Hunan
University, 410082 Changsha, China
A mixture of a-bromo-1-(4-hydroxyphenyl)-1-pentone (0.01
mol) and thiourea (0.01 mol) in ethanol (50 mL) was
refluxed for 3 h. Then the excess solvent was evaporated to
give a yellow solid, which was recrystallized from ethanol
to obtain compound (2) in 71.3% yield, m.p.: 165–166 °C.
1H NMR (CD3SOCD3, ppm) d: 0.87 (t, J = 7.6 Hz, 3H,
CH3), 1.54 (m, 2H, CH2), 2.58 (t, J = 7.6 Hz, 2H, CH2),
6.89 (d, J = 8.8 Hz, 2H, C6H4 3,5-H), 7.29 (d, J = 8.8 Hz,
2H, C6H4 2,6-H), 8.83 (br, 2H, NH2), 9.92 (s, 1H, OH). IR
e-mail: axhu0731@yahoo.com.cn
L.-M. He
College of Pharmacy, Guangdong Pharmaceutical University,
510006 Guangzhou, China
G. Cao
School of Chemistry and Chemical Engineering, Guangdong
Pharmaceutical University, 510006 Guangzhou, China
123
He, Li-Min
