Asian Journal of Chemistry; Vol. 26, No. 7 (2014), 1988-1990
ASIAN JOURNAL OF CHEMISTRY
Synthesis, Crystal Structure and Insecticidal Activity of
1-[2-(3-Ethyl-2,2-dimethylcyclobutyl)acetyl]-3-o-tolylthiourea
1,*
2
1
3
1
YAN-BAI YIN , JIA HAN , YA-LI ZHANG , ZHAN-QIAN SONG and TAO LIU
1Jining Institute of Supervision & Inspection on Product Quality, Jining 272000, P.R. China
2Guohong Chemical Co., Ltd., Yankuang Group, Jining 273512, P.R. China
3Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, P.R. China
*Corresponding author: E-mail: fenghzongyuzhe@163.com
Received: 9 April 2013;
Accepted: 21 June 2013;
Published online: 22 March 2014;
AJC-14943
The compound 1-[2-(3-ethyl-2, 2-dimethylcyclobutyl)acetyl]-3-o-tolylthiourea has been synthesized and its structure was characterized
by IR, 1H NMR and single crystal X-ray diffraction. The crystal belongs to monoclinic system, space group P21/c, a = 14.335(3) Å, b =
9.7100(19) Å, c = 26.737(5) Å, α = 90°, β = 92.70(3)°, γ = 90°, V = 3717.5(13) Å3, Z = 4, µ = 0.178 mm-1, Dc = 1.138 g/cm3, F(000) =
1376, R = 0.0921, wR2 = 0.1379, formula unit C18H26N2OS. Present compound has a fragment of 2,2-dimethylcyclobutane and its
conformation represents semi-chair. The intermolecular and intramolecular hydrogen bonds are revealed. Its insecticidal activity against
Ostrinia furnacalis was also reported in this work.
Keywords: Synthesis, Single crystal X-ray diffraction, Crystal structure, Insecticidal activity.
temperature. o-Toluidine (3.10 g, 0.029 mol) was added into
the mixture. The reaction mixture was refluxed for 7 h. Then
the excessive solution was removed by decompression disti-
llation and the residue was poured into water (70 mL). Finally
pumping filtration left the crude product as yellow powder.
The solid was purified by recrystallization with ethanol in 85.6
% yield. m.p.: 87.2-88.4 °C. IR (KBr, νmax, cm-1): (N-H) 3169,
(C=H) 3025, (C=O) 1686, (C-N) 1254, (C=S) 1151. 1H NMR
(400 MHz, CDCl3, δ): 11.99 (s, 1H, NH), 8.63 (s, 1H, NH),
7.69 (d, 2H, C6H4-), 7.24(m, 2H, C6H4-), 2.50, 2.23 (m, 2H,
CH2), 2.39, 2.19 (m, 2H, CH2), 2.30 (s, 3H, CH3), 1.79 (m,
2H, CH2) , 1.36 (s, 1H, CH), 1.23 (s, 1H, CH), 1.10-0.92 (q,
6H, CH3) , 0.81 (m, 3H, CH3).
INTRODUCTION
Many thiourea compounds exhibit strong structure
stabilization and interesting biological activities. In recent years
the synthesis and their biological activities have been studied.
Many cyclobutyl analogues also have favourable bioacti-
vities1,2. So the thiourea compounds containing cyclobutane
ring may have interesting biological activities. In the study
the application of cyclobutane ring is arranged into the structure
of thiourea compounds to improve their properties and biolo-
gical activities. In this paper, we reported the synthesis of 1-
[2-(3-ethyl-2,2-dimethylcyclobutyl)acetyl]-3-o-tolylthiourea
and its insecticidal activities against Ostrinia furnacalis.
EXPERIMENTAL
Structure determination: A yellow single crystal of the
title compound with dimensions of 0.30 mm × 0.20 mm ×
0.10 mm was mounted on a ENRAF-NONIONS CAD4
equipped with a graphite-monochromatic MoKα radiation (λ
= 0.71073 Å) for data collection at 293(2) K. A total of 7036
reflections including 6631 independent ones (Rint = 0.0995)
were obtained in the range of 1.42 < θ < 25.33, of which 2622
with I > 2σ(I) were considered as observed and used in the
succeeding refinements. The final R = 0.0921 and wR = 0.1379
Preparation of the title compound: The synthesis of the
compound has been performed according to the scheme shown
in Fig. 1. 2,2-Dimethyl-3-ethylcyclobutaneacetic acid was
prepared in our laboratory according to literature3. The title
compound was synthesized according to following method.
2,2-Dimethyl-3-ethylcyclobutaneacetic acid (5 g, 0.029
mol) was dissolved in the mixture of dichloromethane (40 mL)
and SOCl2 (4.5 mL, 0.062 mol). The mixture was stirred and
refluxed for 4 h. Then the excessive solution was removed by
decompression distillation. The residue was added dropwise
to the mixture of KSCN (3.0 g, 0.030 mol) and acetonitrile
(30 mL). The resulting mixture was stirred for 4 h at room
(w = 1/[σ2(Fo2) + (0.0500P)2 + 0.0000P], where P = (Fo2
+
2Fc2)/3), S = 1.009 and (∆/σ)max = 0.000. The maximum and
minimum peaks in the final difference Fourier map are 0.344
and -0.225 e/Å3, respectively.
Yin, Yan-Bai
