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596 JOURNAL OF CHEMICAL RESEARCH 2016
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174–175 °C (lit.16 m.p. 173–174 °C); H NMR (500 MHz, DMSO-d6):
4-Bromothiophene-2-carboxamide (Table 2, entry 15). The residue
was purified by column chromatography (hexanes/EtOAc = 1:1) to
give 4-bromothiophene-2-carboxamide (937 mg, 91%) as a white
δ 7.94 (br. s, 1H), 7.32 (br. s, 1H), 7.21 (s, 2H), 3.81 (s, 6H), 3.69 (s, 3H).
4-Nitrobenzamide (Table 2, entry 6). The residue was purified
by column chromatography (hexanes/EtOAc
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solid, m.p. 154–155 °C (lit.22 m.p. 153–154 °C); H NMR (500 MHz,
= 2:1) to give
4-nitrobenzamide (631 mg, 76%) as a white solid, m.p. 198–200 °C
DMSO-d6): δ 8.02 (br. s, 1H), 7.86 (d, 1H, J = 1.2 Hz), 7.76 (d, 1H,
J = 1.4 Hz), 7.55 (br. s, 1H).
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(lit.16 m.p. 199 °C); H NMR (400 MHz, DMSO-d6): δ 8.33–8.30 (m,
3H), 8.11 (d, 2H, J = 8.4 Hz), 7.74 (br. s, 1H).
4-Fluorobenzamide (Table 2, entry 7). The residue was purified
Acknowledgements
by column chromatography (hexanes/EtOAc
= 1:5) to give
Financial support from the Innovation Project for Graduate
Student of Jiangsu Province (Grant No. CXZZ13-0217) and the
Doctor Project of Guizhou Education University (14BS011) is
gratefully acknowledged.
4-fluorobenzamide (591 mg, 85%) as a white solid, m.p. 153–154 °C
(lit.16 m.p. 153 °C); 1H NMR (500 MHz, DMSO-d6): δ 7.96 (br. s, 1H),
7.92 (m, 2H), 7.35 (br. s, 1H), 7.25 (m, 2H).
Isonicotinamide (Table 2, entry 8). The residue was purified
by column chromatography (hexanes/EtOAc
= 1:3) to give
Electronic Supplementary Information
isonicotinamide (500 mg, 82%) as a white solid, m.p. 157–158 °C
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(lit.19 m.p. 158 °C); H NMR (400 MHz, DMSO-d6): δ 8.72 (d, 2H,
Supplementary data are available through:
J = 6.0 Hz), 8.25 (br. s, 1H), 7.76 (d, 2H, J = 6.0 Hz), 7.74 (br. s, 1H).
Dodecanamide (Table 2, entry 9). The residue was purified by
column chromatography (hexanes/EtOAc = 1:2) to give dodecanamide
(786 mg, 79%) as a white solid, m.p. 101–102 °C (lit.20 m.p.
101–102 °C); 1H NMR (400 MHz, DMSO-d6): δ 7.22 (br. s, 1H), 6.68
(br. s, 1H), 2.02 (t, 2H), 1.46 (m, 2H), 1.29–1.25 (m, 16H), 0.87 (t, 3H).
Octanamide (Table 2, entry 10). The residue was purified by column
chromatography (hexanes/EtOAc = 1:3) to give octanamide (572 mg,
stl.publisher.ingentaconnect.com/content/stl/jcr/supp-data
Received 5 June 2016; accepted 26 July 2016
Paper 1604130 doi: 10.3184/174751916X14737790864571
Published online: 23 September 2016
References
1
C.E. Mabermann, Encyclopedia of Chemical Technology, ed. J.I.
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M.B. Smith and J. March, Advanced Organic Chemistry, 5th edn, John
Wiley & Sons, New York, 2001, Vol. 9, pp. 1415.
1
80%) as a white solid, m.p. 105–106 °C (lit.15 m.p. 105 °C); H NMR
(500 MHz, DMSO-d6): δ 7.18 (br. s, 1H), 6.63 (br. s, 1H), 1.99 (t, 2H,
J = 7.4 Hz), 1.45 (m, 2H), 1.27–1.22 (m, 8H), 0.84 (t, 3H, J = 6.4 Hz).
2-Furoamide (Table 2, entry 11). The residue was purified by column
chromatography (hexanes/EtOAc = 1:2) to give 2-furoamide (516 mg,
2
3
4
5
H. Fujiwara, Y. Ogasawara, K. Yamaguchi and N. Mizuno, Angew. Chem.
Int. Ed., 2007, 46, 5202.
1
93%) as a white solid, m.p. 140–141 °C (lit.16 m.p. 140 °C); H NMR
(400 MHz, DMSO-d6): δ 7.81 (d, 1H, J = 0.8 Hz), 7.79 (br. s, 1H), 7.40
(br. s, 1H), 7.10 (d, 1H, J = 3.2 Hz), 6.61 (m, 1H).
6
7
D. Gnanamgari and R.H. Crabtree, Organometallics, 2009, 28, 922.
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5-Methylfuran-2-carboxamide (Table 2, entry 12). The residue was
purified by column chromatography (hexanes/EtOAc = 1:2) to give
5-methylfuran-2-carboxamide (581 mg, 93%) as a white solid, m.p.
131–132 °C (lit.21 m.p. 131–132 °C). 1H NMR (500 MHz, DMSO-d6):
δ 7.57 (br. s, 1H), 7.18 (br. s, 1H), 6.95 (d, 1H, J = 3.3 Hz), 6.19 (d, 1H,
J = 2.6 Hz), 2.29 (s, 3H).
8
9
G. Saidulu, N. Anand, K.S.R. Rao, A. Burri, S.-E. Park and D.R. Burri,
Catal. Lett., 2011, 141, 1865.
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Lapkin, P. Plucinski, R.J. Watson and J.M.J. Williams, Tetrahedron Lett.,
2011, 52, 4252.
Thiophene-2-carboxamide (Table 2, entry 13). The residue was
purified by column chromatography (hexanes/EtOAc = 1:1) to give
thiophene-2-carboxamide (572 mg, 90%) as a white solid, m.p.
10 A. Martinez-Asencio, M. Yus and D.J. Ramon, Tetrahedron, 2012, 68,
3948.
11 S. Rostamnia, N. Nouruzi, H. Xin and R. Luque, Catal. Sci. Technol., 2015,
5, 199.
12 M. Mamaghani, F. Shirini, M. Sheykhan and M. Mohsenimehr, RSC Adv.,
2015, 5, 44524.
1
178–179 °C (lit.16 m.p. 178 °C); H NMR (400 MHz, DMSO-d6): δ
7.97 (br. s, 1H), 7.74 (d, 2H, J = 4.0 Hz), 7.39 (br. s, 1H), 7.13 (t, 1H,
J = 4.0 Hz).
5-Methylthiophene-2-carboxamide (Table 2, entry 14). The residue
was purified by column chromatography (hexanes/EtOAc = 1:2) to
give 5-methylthiophene-2-carboxamide (649 mg, 92%) as a white
13 D.K. Kurhe and R.V. Jayaram, Catal. Commun., 2014, 57, 69.
14 M. Kim, J. Lee, H.-Y. Lee and S. Chang, Adv. Synth. Catal., 2009, 351,
1807.
15 J. Lee, M. Kim, S. Chang and H.-Y. Lee, Org. Lett., 2009, 11, 5598.
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20 R.M. Gipson, F.H. Pettit, C.G. Skinner and W. Shive, J. Org. Chem., 1963,
28, 1425.
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solid, m.p. 162–163 °C; H NMR (500 MHz, DMSO-d6): δ 7.80 (br.
s, 1H, CONH2), 7.51 (d, 1H, J = 3.6 Hz, CH–C–CONH2), 7.22 (br.
s, 1H, CONH2), 6.79 (m, 1H, CH–C–CH3), 2.42 (s, 3H, C–CH3);
13C NMR (500 MHz, DMSO-d6): δ 162.9 (CONH2), 144.8 (C–CH3),
137.8 (C–CONH2), 128.9 (CH–C–CONH2), 126.4 (CH–C–CH3), 15.2
(C–CH3); MS (ESI+): 142.0 [M+H]+; Elemental analysis calcd (%) for
C6H7NOS: C, 51.04; H, 5.00; N, 9.92; S, 22.71; found: C, 51.13; H, 5.04;
N, 9.89; S, 22.72.
21 K. Kawabe, T. Suzuil and M. Iguchi, Yakugaku Zasshi, 1960, 80, 58.
22 P. Fournari, R. Guilard and M. Person, Bull. Soc. Chim. Fr., 1967, 4115.