Yao & Wei
FULL PAPER
145-4, 1305, 1253, 1124, 1040, 917, 754, 709, 638, 52+1
cm 1; HRMS (EI) calcd for C14H14NO2 [M+H]
228.1026, found 228.1062.
(s, 3H), 2.44 (s, 3H); 13C NMR (CDCl3, 75 MHz) δ:
164.5, 155.4, 141.0, 131.0, 130.0, 128.3, 125.9, 121.0,
113.1, 54.4, 20.4; IR (KBr) v: 3338, 1648, 1519, 1415,
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N-Benzoylbenzocaine (3f) White solid (126 mg,
1253, 1182, 1035, 826, 749, 670, 554, 521 cm .
1
94%); H NMR (CDCl3, 300 MHz) δ: 8.07 (d, J=8.7
N-(4-Methylphenyl)-toluamide (3m) White solid
(108 mg, 96%); 1H NMR (CDCl3, 300 MHz) δ: 7.76 (d,
J=7.8 Hz, 3H), 7.52 (d, J=7.8 Hz, 2H), 7.27 (d, J=
7.2 Hz, 2H), 7.17 (d, J=7.8 Hz, 2H), 2.43 (s, 3H), 2.35
(s, 3H); 13C NMR (CDCl3, 75 MHz) δ: 164.8, 140.9,
134.5, 132.9, 131.1, 128.4, 128.2, 126.0, 119.4, 20.4,
19.8; IR (KBr) v: 3351, 1648, 1596, 1519, 1402, 1318,
Hz, 2H), 7.98 (s, 1H), 7.88 (d, J=7.0 Hz, 2H), 7.74 (d,
J=8.7 Hz, 2H), 7.59—7.50 (m, 3H), 4.39 (q, J=7.1 Hz,
2H), 1.41 (t, J=7.1 Hz, 3H); 13C NMR (CDCl3, 75
MHz) δ: 165.2, 164.9, 141.1, 133.4, 131.0, 129.7, 127.7,
126.0, 125.0, 118.2, 59.8, 13.2; IR (KBr) v: 3344, 1712,
1649, 1603, 1531, 1409, 1272, 1182, 1110, 1033, 852,
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-1
768, 690, 651, 502 cm .
1247, 1105, 891, 812, 760, 658, 502 cm .
N-(4-Chlorophenyl)-benzamide (3g) White solid
N-Phenylacetamide (3n) White solid (55 mg,
1
1
(111 mg, 96%); H NMR (CDCl3, 300 MHz) δ: 7.88—
81%); H NMR (CDCl3, 300 MHz) δ: 7.49 (d, J=7.4
7.86 (d, J=7.4 Hz, 2H), 7.82 (s, 1H), 7.63—7.48 (m,
5H), 7.36 — 7.33 (d, J = 10.3 Hz, 2H); 13C NMR
(DMSO-d6, 75 MHz) δ: 165.0, 137.5, 134.1, 131.0,
127.9, 127.7, 127.0, 126.6, 121.2; IR (KBr) v: 3351,
1649, 1603, 1519, 1486, 1396, 1312, 1091, 1007, 819,
Hz, 2H), 7.36—7.27 (m, 3H), 7.12 (t, J=7.4 Hz, 1H),
2.20 (s, 3H); 13C NMR (CDCl3, 75 MHz) δ: 168.7,
137.9, 128.9, 124.3, 120.0, 24.6; IR (KBr) v: 3293, 1663,
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1593, 1543, 1434, 1314, 755, 515 cm .
N-(4-Methoxyphenyl)-acetamide (3o)
White
-1
1
722, 638, 509 cm .
solid (71 mg, 86%); H NMR (CDCl3, 300 MHz) δ:
7.39 (d, J=7.2 Hz, 2H), 7.11 (s, 1H), 6.86 (d, J=7.1
Hz, 2H), 3.78 (s, 3H), 2.15 (s, 3H); 13C NMR (CDCl3,
75 MHz) δ: 168.6, 156.3, 131.0, 122.0, 114.0, 55.5, 24.3;
IR (KBr) v: 3270, 165-3, 1573, 1514, 1314, 1254, 1035,
N-(4-Bromophenyl)-benzamide (3h) White solid
(113 mg, 82%); 1H NMR (CDCl3, 300 MHz) δ: 7.84 (d,
J=7.2 Hz, 2H), 7.79 (s, 1H), 7.56—7.46 (m, 7H); 13C
NMR (DMSO-d6, 75 MHz) δ: 166.1, 139.0, 135.2,
132.2, 131.9, 128.9, 128.2, 122.6, 115.8; IR (KBr) v:
3388, 1648, 1596, 1525, 1486, 1389, 1312, 1072, 1014,
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835, 755, 615, 536 cm .
N-(4-Methylphenyl)-acetamide (3p) White solid
- 1
1
819, 722, 651, 515+ cm ; HRMS (EI) calcd for
(70 mg, 94%); H NMR (CDCl3, 300 MHz) δ: 7.34 (d,
C13H11NOBr [M+H] 278.0004, found 278.0006.
N-(2-Aminophenyl)-benzamide (3i) White solid
(100 mg, 95%); 1H NMR (CDCl3, 300 MHz) δ: 7.91 (d,
J=6.6 Hz, 2H), 7.86 (s, 1H), 7.58—7.50 (m, 3H), 7.34
(d, J=6.8 Hz, 1H), 7.12 (t, J=7.2 Hz, 1H), 6.88 (m,
2H), 3.89 (s, 2H); 13C NMR (CDCl3, 75 MHz) δ: 164.8,
139.7, 133.1, 130.8, 127.6, 126.2, 126.1, 124.2, 123.4,
118.6, 117.2; IR (KBr) v: 3273, 1648, 1531, 1505, 1440,
J=8.1 Hz, 2H), 7.10 (d, J=7.8 Hz, 3H), 2.30 (s, 3H),
2.16 (s, 3H); 13C NMR (CDCl3, 75 MHz) δ: 168.6,
135.3, 133.9, 129.5, 24.5, 20.9; IR (KBr) v: 3290, 1650,
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1554, 1503, 1401, 1324, 1024, 835, 755, 515 cm .
N-(4-Bromophenyl)-acetamide (3q) White solid
1
(85 mg, 80%); H NMR (DMSO-d6, 300 MHz) δ: 10.0
(s, 1H), 7.54 (d, J=8.4 Hz, 2H), 7.44 (d, J=8.4 Hz,
2H), 2.03 (s, 3H); 13C NMR (CDCl3, 75 MHz) δ: 167.8,
138.0, 130.8, 120.2, 113.8, 23.4; IR (KBr) v: 3300, 1674,
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1318, 1163, 910, 761, 703, 605 cm ; HRMS (EI) calcd
for C13H13N2O [M+H]+ 213.1030, found 213.1034.
N-(2-Pyridinyl)-benzamide (3j) White solid (93
mg, 94%); 1H NMR (CDCl3, 300 MHz) δ: 8.94 (s, 1H),
8.38 (d, J=8.3 Hz, 1H), 8.20 (s, 1H), 7.90 (d, J=7.1
Hz, 2H), 7.77—7.72 (m, 1H), 7.58—7.45 (m, 3H), 7.04
(t, J=6.8 Hz, 1H); 13C NMR (CDCl3, 75 MHz) δ: 166.4,
151.9, 147.7, 138.5, 134.5, 132.1, 128.7, 127.5, 119.8,
114.5; IR (KBr) v: 3189, 1670, 1577, 15-25, 1435, 1305,
1596, 1533, 1394, 1314, 1241, 994, 825, 725, 496 cm .
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N-Acetylbenzocaine (3r) White solid (99 mg,
1
96%); H NMR (CDCl3, 300 MHz) δ: 8.00 (d, J=8.2
Hz, 2H), 7.58 (d, J=8.2 Hz, 2H), 7.43 (s, 1H), 4.38 (q,
J=7.0 Hz, 2H), 2.22 (s, 3H), 1.40 (t, J=7.1 Hz, 3H);
13C NMR (CDCl3, 75 MHz) δ: 168.0, 165.3, 141.2,
129.6, 124.6, 117.9, 59.8, 24.5, 13.2; IR (KBr) v: 3338,
1701, 1677, 1596, 1519, 1370, 1305, 1178, 1124, 1008,
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1156, 903, 787, 717, 684, 612, 502 cm ; HRMS (EI)
865, 774, 709, 593 cm .
calcd for C12H11N2O [M + H] + 200.0906, found
N-(2-Methoxyphenyl)-acetamide (3s)
White
1
200.0908.
solid (75 mg, 91%); H NMR (CDCl3, 300 MHz) δ:
8.36 (d, J=7.8 Hz, 1H), 7.77 (s, 1H), 7.08—6.95 (m,
2H), 6.88 (d, J=7.9 Hz, 1H), 3.90 (s, 3H), 2.22 (s, 3H);
13C NMR (CDCl3, 75 MHz) δ: 168.2, 147.7, 127.6,
123.6, 120.9, 119.8, 109.9, 55.6, 24.8; IR (KBr) v: 3254,
1654, 1596,-1544, 1486, 1363, 1253, 1177, 1020, 749,
N-(2-Thienyl)-benzamide (3k) White solid (91
mg, 90%); 1H NMR (CDCl3, 300 MHz) δ: 8.59 (s, 1H),
7.90 (d, J=7.1 Hz, 2H), 7.62—7.49 (m, 3H), 6.98—
6.90 (m, 2H), 6.81 (d, J=2.4 Hz, 1H); 13C NMR
(CDCl3, 75 MHz) δ: 163.9, 139.2, 133.1, 132.1, 128.8,
127.1, 123.9, 118.3, 112.4; IR (KBr) v: 3230, 1644,
1
658, 521 cm .
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1563, 1494, 1364, 1304, 895, 815, 703 cm .
N-(2-Methylphenyl)-acetamide (3t) White solid
1
N-(4-Methoxyphenyl)-toluamide (3l) White solid
(118 mg, 98%); 1H NMR (CDCl3, 300 MHz) δ: 7.76 (d,
J=7.6 Hz, 2H), 7.73 (s, 1H), 7.54 (d, J=8.3 Hz, 2H),
7.28 (d, J=8.3 Hz, 2H), 6.91 (d, J=8.5 Hz, 2H), 3.83
(62 mg, 81%); H NMR (CDCl3, 300 MHz) δ: 7.73 (d,
J=7.7 Hz, 1H), 7.25—7.17 (m, 3H), 7.10—7.01 (m,
2H), 2.25 (s, 3H), 2.20 (s, 3H); 13C NMR (CDCl3, 75
MHz) δ: 169.0, 135.6, 130.5, 127.9, 127.0, 126.5, 124.2,
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© 2010 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2010, 28, 2260—2268