A. Souldozi et al. · Synthesis and Single Crystal X-Ray Structure of 2-(1,3,4-Oxadiazol-2-yl)aniline
839
recorded on a FINNIGAN-MAT 8430 mass spectrome- Preparation of single crystals of 2-(1,3,4-oxadiazol-2-yl)-
ter operating at an ionization potential of 20 eV. Melting aniline (5)
points were measured on an Electrothermal 9100 apparatus
and are uncorrected. (N-Isocyanimino)triphenylphosphorane
Single crystals of 5 were prepared by using the branch
◦
tube method with n-hexane at 40 C during two weeks [30].
(
2) was prepared based on a reported procedure [17].
The light yellow crystals were filtered off, washed with cold
Other starting materials and solvents were obtained
from Merck (Germany) and Fluka (Switzerland) and
were used without further purification. Flash chromato-
graphy columns were prepared from Merck silica gel
powder.
◦
n-hexane and dried at r. t. (m. p. 145.5 C).
Crystal structure determination of 5
The crystallographic measurement was performed on a
κ-geometry Kuma KM4CCD automated four-circle diffrac-
tometer with the graphite-monochromatized MoKα radia-
tion. The data were collected at 100(2) K using the Ox-
ford Cryosystems cooler. A summary of the conditions for
the data collection and the structure refinement parameters
is given in Table 1. The data were corrected for Lorentz and
polarization effects. Data collection, cell refinement, and data
reduction and analysis were carried out with the KM4CCD
software (Oxford Diffraction, Poland): CrysAlis CCD and
CrysAlis RED, respectively [31]. The structure was solved by
Direct Methods using SHELXS-97 [32] and refined by full-
matrix least-squares techniques with anisotropic displace-
ment parameters for the non-H atoms using SHELXL-97 [33].
All H atoms were found in difference Fourier maps and were
refined isotropically. All figures were made using the pro-
gram XP [34].
2-(1,3,4-Oxadiazol-2-yl)aniline (5)
To a magnetically stirred solution of (N-isocyanimino)
triphenylphosphorane 2 (0.302 g, 1 mmol) in dry CH Cl
2
2
(
8 mL) was added dropwise a mixture of 2-amino ben-
zoic acid 1 (0.137 g, 1 mmol) in dry CH Cl (7 mL) over
2
2
15 min. The mixture was stirred for 6 h at r. t. The sol-
vent was removed under reduced pressure and the viscous
residue was purified by flash column chromatography [silica
gel; petroleum ether-ethyl acetate (10 : 2)]. The solvent was
removed under reduced pressure and the product 4 was ob-
tained as light yellow crystals. Yield: 140 mg (86 %); m. p.
◦
1
2
45.3 C. – IR (KBr): ν = 3431, 3339, 3039, 2939, 2931,
−1
1
931, 1623, 1269, 1108, 754 cm . – H NMR (CDCl ):
3
δ = 5.69 (br. s, 2 H, NH ), 6.73 (s, 1 H, arom.), 6.79
2
3
3
Supplementary material
(
t, 1 H, J = 7.5 Hz, arom.), 7.75 (t, 1 H, J = 7.8 Hz,
3
arom.), 7.76 (d, 1 H, J = 6.0 Hz, arom.), 8.41 (s, 1 H, oxa-
CCDC 635760 contains the supplementary crystallo-
1
3
diazole). – C NMR (CDCl ): δ = 116.28, 116.91, 127.99 graphic data for this paper. These data can be obtained free
3
and 132.79 (4 CH, arom.); 105.38 and 147.01 (2 C, arom.); of charge from The Cambridge Crystallographic Data Centre
1
50.91 (1 CH, oxadiazole); 164.62 (1 C, oxadiazole). – MS: via www.ccdc.cam.ac.uk/data request/cif.
+
m/z (%) = 161 (100) [M] , 120 (50), 105 (22), 92 (25), 90
Acknowledgement
(
(
15), 78 (15), 77 ( 34), 65 (28), 63 (21), 58 (22), 55 (11), 52
20), 51 (31), 50 (18), 43 (28), 41 (21). – C H N O (161.06):
The Iranian authors are thankful to the Research Council
8
7 3
calcd. C 59.62, H 4.38, N 26.07; found C 59.57, H 4.34, of the Urmia Islamic Azad University for partial support of
N 26.14.
this work.
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