Page 7 of 7
RSC Advances
DOI: 10.1039/C5RA11721F
to give 4 in 74% (0.74 g) yield as gummy product. 1H NMR
(CDCl3, 400 MHz): δ 8.31 (s, 1H), 8.15 (d, 1H, J = 4.4 Hz), 8.11
K. M. Anderson, N. Clarke and J. W. Steed, New J. Chem., 2010, 34,
2261.
(s, 1H), 8.03 (d, 1H, J = 8 Hz), 7.18 – 7.17 (m, 1H), 5.69 (br t, 7. M. Haldimann, B. Zimmerli, C. Als and H. Gerber, Clin. Chem., 1998,
1H), 3.25 – 3.20 (m, 2H), 1.50 – 1.43 (m, 2H), 1.37 – 1.27 (m,
2H), 0.88 (t, 3H, J = 8 Hz); 13C NMR (CDCl3, 100 MHz): 156.5,
142.8, 140.2, 136.8, 126.4, 123.8, 39.8, 32.1, 20.0, 13.7; FTIR
(KBr) ν cmꢀ1: 3296, 2931, 1669, 1534, 1474, 1275; Anal Calcd
for C10H15N3O: C, 62.15, H, 7.82, N, 21.74. Found: C, 62.21, H,
7.91, N, 21.59.
44, 817 and references cited therein.
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R. A. J. Janssen and E. W. Meijer, Angew. Chem. Int. Ed., 2001, 40,
3660.
N, N׳
ꢀHexyleneꢀ1,6ꢀdiylbis(N׳
ꢀpyridinꢀ3ꢀylurea) (5):6c
To a stirred solution of 1, 6ꢀdiisocyanatoꢀhexane (0.5 g, 2.93 10. F. Fages, in Molecular Gels, eds. R. Weiss and P. Terech, Springer
mmol) in 15 mL dry CH2Cl2 , a mixture of 3ꢀaminopyridine (0.83 Netherlands, 2006, DOI: 10.1007/1ꢀ4020ꢀ3689ꢀ2ꢀ24, ch. 24, pp. 793ꢀ815.
g, 8.92 mmol) and Et3N (0.94 mL, 7.32 mmol) dissolved in 20 11. D. K. Kumar, D. Amilan Jose, A. Das and P. Dastidar, Chem. Commun.,
mL CH2Cl2 was added and the reaction mixture was allowed to 2005, 4059
stir for 24 h. After completion of reaction, a white precipitate 12. B. K. An, S. K. Kwon, S. D. Jung and S. Y. Park, J. Am. Chem. Soc.,
appeared which was filtered off and washed with warm CH2Cl2
2002, 124, 14410; (b) Y. Chen, Y. Lv, Y. Han, B. Zhu, F. Zhang, Z. Bo
and C. –Y. Liu, Langmuir, 2009, 25, 8548; (c) H. Yang, T. Yi, Z. Zhou, J.
Wu, M. Xu, F. Li and C. Huang, Langmuir, 2007, 23, 8224.
13. A. Kearvell and F. Wilkinson, Molecular Crystals, 1968, 4, 69.
14. D. G. Whitten, Acc. Chem. Res., 1993, 26, 502.
followed by diethyl ether to have pure compound 5 in 72% yield
0
1
(0.76 g, mp 184ꢀ186 C); H NMR (CDCl3 containing one drop
of DMSOꢀd6, 400 MHz): δ 8.44 (d, 2H, J = 4 Hz), 8.27 (s, 2H),
8.13 (dd, 2H, J1 = 8 Hz, J2 = 4 Hz), 8.03 (dd, 2H, J1 = 8 Hz, J2 =
4 Hz), 7.18 – 7.15 (m, 2H), 5.93 (br t, 2H), 3.20 (q, 4H, J = 8
Hz), 1.54 – 1.51 (m, 4H), 1.21 – 1.19 (m, 4H); FTIR (KBr) ν cmꢀ
1: 3337, 2931, 1638, 1564, 1119; Mass (EI): 357.2 (M +1)+.
15. X. Cai, K. Liu, J. Yan, H. Zhang, X. Hou, Z. Liu and Y. Fang, Soft
Matter, 2012, 8, 3756.
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W. Moon, S. W. Ko, J. Y. Lee, S. K. Kim, J. Yoon and K. C. Nam, J. Am.
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