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NMR (100 MHz, CDCl3): d 160.45, 139.01, 136.60, 134.55,
129.42, 128.79, 128.49, 127.94, 127.04, 64.84; anal. calcd for
Notes and references
C
14H12ClN: C 73.20, H 5.27, N, 6.10; found C 73.46, H 5.51, N
6.48.
N-(3-Bromobenzylidene)-1-phenylmethanamine (4e). Yield
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99%; colourless liquid; IR (KBr): 3061, 3028, 2844, 1700, 1644,
1565, 1453, 1425, 1210, 1065, 783, 698 cmꢂ1; 1H NMR (400 MHz,
CDCl3): d 8.33 (s, 1H), 8.01 (d, J ¼ 1.6 Hz, 1H), 7.69–7.67 (m, 1H),
7.57–7.55 (m, 1H), 7.41–7.38 (m, 4H), 7.32–7.27 (m, 2H), 4.85 (s,
2H); 13C NMR (100 MHz, CDCl3): d 160.11, 138.82, 138.06,
133.49, 130.74, 130.01, 128.46, 127.91, 127.03, 126.96, 122.82,
64.85; anal. calcd for C14H12BrN: C 61.33, H 4.41, N 5.11; found
C 61.56, H 4.70, N 5.49.
1-(4-Methoxyphenyl)-N-(2-methylbenzylidene)-methanamine
(4f). Yield 95%; colourless liquid; IR (KBr): 3406, 3003, 2932,
2835, 1635, 1606, 1512, 1247, 1174, 1034 cmꢂ1; H NMR (400
1
MHz, CDCl3): d 8.71 (s, 1H), 7.96–7.94 (m, 1H), 7.35–7.20 (m,
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5H), 6.94–6.90 (m, 2H), 4.81 (s, 2H), 3.82 (s, 3H), 2.53 (s, 3H); 13
C
NMR (100 MHz, CDCl3): d 160.33, 158.74, 137.71, 134.25,
130.87, 130.37, 129.18, 127.71, 126.27, 114.06, 114.00, 65.09,
55.37, 19.43; anal. calcd for C16H17NO: C 80.30, H 7.16, N, 5.85;
found C 80.07, H 7.27, N 5.76.
10 A. Duschek and S. F. Kirsch, Angew. Chem., Int. Ed., 2011, 50,
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4156.
2-(2-Chloro-6-methylphenyl)-1H-benzo[d]imidazole (6c).
Yield 85%; colourless solid; mp 247–248 ꢁC; IR (KBr): 3417,
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7277–7287.
13 D. Macikenas, E. Skrzypczak-Jankun and J. D. Protasiewicz,
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B. P. Rempel, M. J. Ferguson and R. R. Tykwinski, Angew.
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18 U. Ladziata, A. Y. Koposov, K. Y. Lo, J. Willging,
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1
2923, 2852, 1632, 1454, 1260, 1013 cmꢂ1; H NMR (400 MHz,
CDCl3): d 7.50–7.47 (m, 2H), 7.27–7.11 (m, 4H), 7.11–7.09 (m,
1H), 2.06 (s, 3H); 13C NMR (100 MHz, CDCl3): d 149.05, 140.94,
138.17, 134.56, 130.75, 129.98, 128.67, 127.03, 122.86, 115.36,
20.32; HRMS (ESI-TOF) calculated for C14H12ClN2 (MH+)
243.0689, found 243.0672; anal. calcd for C14H11ClN2: C 69.28,
H 4.57, N 11.54; found C 70.11, H 4.45, N 11.72.
2-(2-Bromo-5-uorophenyl)-1H-benzo[d]imidazole (6d).
Yield 86%; colourless solid; mp 139–143 ꢁC; IR (KBr): 3438,
2924, 2853, 1633, 1465, 1260, 741 cmꢂ1 1H NMR (400 MHz,
;
CDCl3): d 8.08–8.02 (m, 4H), 7.47–7.43 (m, 2H), 7.23–7.18 (m,
2H); 13C NMR (100 MHz, CDCl3): d 141.97, 139.77, 135.85,
135.03, 133.84, 133.47, 132.04, 129.38, 129.25, 128.13, 127.46;
HRMS (ESI-TOF) calculated for C13H9BrFN2 (MH+) 290.9933,
found 290.9960; anal. calcd for C13H8BrFN2: C 53.63, H 2.77, N
9.62; found C 53.82, H 2.93, N 9.51.
19 B. V. Meprathu, M. W. Justik and J. D. Protasiewicz,
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2-(3,5-Dibromo-2,4,6-trimethylphenyl)-1H-benzo[d]imid-
azole (6f). Yield 79%; colourless solid; mp 290–292 ꢁC; IR (KBr):
3437, 1633, 668 cmꢂ1; 1H NMR (400 MHz, CDCl3): d 7.57 (s, 1H),
7.32–7.28 (m, 4H), 2.74 (s, 3H), 2.07 (s, 6H); 13C NMR (100 MHz,
CDCl3): d 150.92, 139.78, 137.29, 130.63, 125.86, 123.15, 26.30,
22.28; HRMS (ESI-TOF) calculated for C16H15Br2N2 (MH+)
392.9602, found 392.9604; anal. calcd for C16H14Br2N2: C 48.76,
H 3.58, N 7.11; found C 48.61, H 3.69, N 7.28.
20 A. Y. Koposov, D. N. Litvinov, V. V. Zhdankin, M. J. Ferguson,
R. McDonald and R. R. Tykwinski, Eur. J. Org. Chem., 2006,
4791–4795.
21 R. D. Richardson, J. M. Zayed, S. Altermann, D. Smith and
T. Wirth, Angew. Chem., Int. Ed., 2007, 46, 6529–
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23 J. N. Moorthy, K. Senapati, K. N. Parida, S. Jhulki, K. Sooraj
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Acknowledgements
We are thankful to DST (New Delhi, India; Grant no. INT/FIN-
LAND/P-06 and SR/S1/IC-59/2010) for nancial support. TKA
and SM are thankful to UGC and CSIR (India), respectively for
fellowship. We are also thankful to Dr C. Giri for his help during
manuscript preparation and IMMT Bhubaneswar for elemental
analysis.
¨
25 M. Mulbaier and A. Giannis, Angew. Chem., Int. Ed., 2001, 40,
4393–4394.
26 K. C. Nicolaou, K. Sugita, P. S. Baran and Y. L. Zhong, J. Am.
Chem. Soc., 2002, 124, 2221–2232.
12838 | RSC Adv., 2014, 4, 12834–12839
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