JOURNAL OF CHEMICAL RESEARCH 2013 625
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to reflux under a nitrogen atmosphere for 2 h. After cooling to room
temperature, the solid was filtered, washed with EtOH and the filtrate
evaporated. The filtered catalyst can be recycled after washing with
CH2Cl2 and drying for 2 h. The crude product was purified by column
chromatography. All the isolated compounds were characterised by
m.p., IR, 1H NMR, 13C NMR and elemental analysis. The physical data
(m.p., IR, NMR) of known compounds were found to be identical with
those reported in the literature.31–34
N-(3-Bromophenyl)urea (Table 2, entry 5): M.p. 166–168 °C; FT-IR
(KBr, cm–1) 3375, 3333, 3189, 1679, 1578, 1476, 1410, 1091, 861, 777, 674,
599; 1H NMR (250 MHz, DMSO-d6) δH =8.74 (s, 1H), 7.83 (s, 1H), 7.23–
7.15 (m, 2H), 7.07 (d, J=8.1 Hz, 1H), 5.97 (s, 2H); 13C NMR (62.5 MHz,
DMSO-d6) δC =156.2, 142.7, 131.0, 123.0, 120.4, 120.2, 116.8; Anal.
Calcd for C7H7N2OBr: C, 39.10; H, 3.28; N, 37.16. Found: C, 39.20; H,
3.34; N, 37.26%.
6
7
8
9
S.-H. Jung and H. Kohn, J. Am. Chem. Soc., 1985, 107, 2931.
10 E. Artuso, I. Degani, R. Fochi and C. Magistris, Synthesis, 2007, 3497.
11 D. Habibi, M. Nasrollahzadeh, H. Sahebekhtiari and R.V. Parish,
Tetrahedron, 2013, 69, 3082.
12 D. Habibi, M. Nasrollahzadeh, A.R. Faraji and Y. Bayat, Tetrahedron,
2010, 66, 3866.
13 D. Habibi, M. Nasrollahzadeh, H. Sahebekhtiari and S.M. Sajadi, Synlett,
2012, 23, 2795.
14 D. Habibi and M. Nasrollahzadeh, Y. Bayat, Synth. Commun., 2011, 41,
2135.
15 D. Habibi and M. Nasrollahzadeh, Synth. Commun., 2010, 40, 3159.
16 D. Habibi and M. Nasrollahzadeh, Synth. Commun., 2012, 42, 2023.
17 D. Habibi and M. Nasrollahzadeh, Monatsh. Chem., 2012, 143, 925.
18 D. Habibi, M. Nasrollahzadeh, A.R. Faraji and Y. Bayat, Tetrahedron,
2010, 66, 3866.
19 M. Nasrollahzadeh, D. Habibi and Z. Shahkarami, Y. Bayat, Tetrahedron,
2009, 51, 10715.
20 D. Habibi, M. Nasrollahzadeh and T.A. Kamali, Green Chem., 2011, 13,
3499.
N-(1-Naphthyl)urea (Table 2, entry 8): M.p. 220–222 °C; FT-IR (KBr,
cm–1) 3444, 33055, 3206, 3052, 2922, 1651, 1608, 1555, 1530, 1505, 1360,
1
1335, 1278, 1101, 785, 772, 608, 530; H NMR (250 MHz, DMSO-d6)
δH =8.70 (s, 1H), 8.17 (s, 1H), 8.00 (d, J=7.3 Hz, 1H), 7.85 (s, 1H), 7.73–
7.37 (m, 4H), 6.22 (s, 2H); 13C NMR (62.5 MHz, DMSO-d6) δC = 157.1,
135.9, 134.5, 128.9, 126.6, 126.4, 126.0, 122.7, 122.3, 117.5; Anal. Calcd
for C11H10N2O2: C, 70.95; H, 5.41; N, 15.04. Found: C, 70.82; H, 5.34; N,
14.91%.
21 D. Habibi, S. Heydari and M. Nasrollahzadeh, J. Chem. Res., 2012, 573.
22 M. Nasrollahzadeh, Y. Bayat, D. Habibi and S. Moshaee, Tetrahedron
Lett., 2009, 50, 4435.
23 D. Habibi, M. Nasrollahzadeh, L. Mehrabi and S. Mostafaee, Monatsh.
Chem., 2013, 144, 725.
We gratefully acknowledge Soran University for support of this
work.
24 D. Habibi, H. Nabavi and M. Nasrollahzadeh, J. Chem., 2013, article ID
645313.
25 D. Habibi, M. Nasrollahzadeh and H. Sahebekhtiari, J. Mol. Catal. A:
Chem., 2013, 378, 148.
26 L. Adak, K. Chattopadhyay and B.C. Ranu, J. Org. Chem., 2009, 74, 3982.
27 R. Juarez, P. Concepcion, A. Corma and H. Garcýa, Chem. Commun.,
2010, 46, 4181.
28 R. Juarez, A. Corma and H. Garcia, Green Chem., 2009, 11, 949.
29 S.M. Agawane and J.M. Nagarkar, Tetrahedron Lett., 2011, 52, 5220.
30 S. Bahari, B. Mohammadi-Aghdam, S.M. Sajadi and F. Zeidali, Bull. Kor.
Chem. Soc., 2012, 33, 2251.
Received 21 June 2013; accepted 6 August 2013
Paper 1302021 doi:10.3184/174751913X13787959859461
Published online: 7 October 2013
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