The Journal of Organic Chemistry
Article
N-(4-Methoxyphenyl)-3,3-diphenylacrylamide (2a). The resultant
residue was purified by flash silica gel column chromatography
(eluent:petroleum ether/EtOAc = 10:1, v/v) to afford 2a as a white
solid (27.1 mg, 82%); mp: 152−154 °C. 1H NMR (400 MHz,
CDCl3): δ 3.73 (s, 3 H), 6.50 (s, 1 H), 6.74 (d, J = 8.8 Hz, 2 H), 6.90
(s, 1 H), 7.03 (d, J = 8.8 Hz, 2 H), 7.31−7.35 (m, 7 H), 7.45−7.46 (m,
3 H). 13C{H} NMR (100 MHz, CDCl3): δ 55.4, 114.0, 121.3, 123.1,
128.0, 128.5, 128.9, 129.0, 129.1, 129.5, 130.7, 138.2, 140.6, 150.0,
156.3, 164.2. HRMS (ESI, m/z): calcd for C22H20NO2: [M + H]+ =
330.1489; found: 330.1483. IR (neat, cm−1):3406, 3280, 2926, 2371,
2253, 1893, 1646, 1599, 1408, 1241,1172, 1038, 908, 836, 733, 649,
531, 455, 438.
N-(3-Methoxyphenyl)-3,3-diphenylacrylamide (2b). The resultant
residue was purified by flash silica gel column chromatography
(eluent:petroleum ether/EtOAc = 10:1, v/v) to afford 2b as a white
solid (28.7 mg, 87%); mp: 116−118 °C. 1H NMR (400 MHz,
CDCl3): δ 3.72 (s, 3 H), 6.49 (s, 1 H), 6.53−6.58 (m, 2 H), 6.92 (s, 1
H), 6.98 (s, 1 H), 7.07 (t, J = 8.0 Hz, 1 H), 7.28−7.35 (m, 7 H), 7.46−
7.47 (m, 3 H). 13C{H} NMR (100 MHz, CDCl3): δ 55.2, 105.1, 110.0,
111.7, 123.0, 128.0, 128.5, 129.0, 129.0, 129.2, 129.4, 129.5, 138.1,
138.8, 140.4, 150.5, 160.0, 164.3. HRMS (ESI, m/z): calcd for
C22H20NO2: [M + H]+ = 330.1489; found: 330.1479. IR (neat, cm−1):
3400, 3303, 2929, 2248, 1954, 1658, 1540, 1293, 1158, 1035, 909, 734,
649, 580, 545, 455.
N-(2-Methoxyphenyl)-3,3-diphenylacrylamide (2c). The resultant
residue was purified by flash silica gel column chromatography
(eluent:petroleum ether/EtOAc = 10:1, v/v) to afford 2c as a colorless
liquid (22.5 mg, 68%). 1H NMR (400 MHz, CDCl3): δ 3.59 (s, 3 H),
6.49 (s, 1 H), 6.72 (dd, J = 1.2, 8.0 Hz, 1 H), 6.87−6.98 (m, 2 H),
7.28−7.35 (m, 7 H), 7.40−7.42 (m, 3 H), 7.71 (s, 1 H), 8.40 (dd, J =
1.2, 8.0 Hz, 1 H). 13C{H} NMR (100 MHz, CDCl3): δ 55.3, 109.6,
119.6, 120.9, 123.3, 123.4, 127.7, 128.2, 128.4, 128.6, 129.0, 129.7,
138.1, 141.1, 147.7, 150.6, 164.2. HRMS (ESI, m/z): calcd for
C22H20NO2: [M + H]+ = 330.1489; found: 330.1481. IR (neat, cm−1):
3395, 2925, 2855, 2373, 1655, 1598, 1460, 1257, 1116, 908, 738, 700,
630, 462.
N-3,3-Triphenylacrylamide (2d). The resultant residue was purified
by flash silica gel column chromatography (eluent:petroleum ether/
EtOAc = 10:1, v/v) to afford 2d as a white solid (21.6 mg, 72%); mp:
114−116 °C. 1H NMR (400 MHz, CD3COCD3): δ 6.60 (s, 1 H), 7.01
(t, J = 7.6 Hz, 1 H), 7.22−7.28 (m, 4 H), 7.31−7.39 (m, 8 H), 7.54 (d,
J = 7.6 Hz, 2 H), 9.00 (s, 1 H). 13C{H} NMR (100 MHz,
CD3COCD3): δ 120.0 120.1, 123.2, 123.3, 124.2, 128.8, 128.8, 128.9,
129.3, 129.5, 129.8, 130.5, 140.1, 140.4, 142.6, 152.3, 164.7. HRMS
(ESI, m/z): calcd for C21H18NO: [M + H]+ = 300.1383; found:
300.1378. IR (neat, cm−1): 3406, 3311, 3057, 2926, 1955, 1655, 1598,
1441, 1313, 1265, 1177, 1029, 738, 699, 579, 510, 457.
N-(4-Ethylphenyl)-3,3-diphenylacrylamide (2g). The resultant
residue was purified by flash silica gel column chromatography
(eluent:petroleum ether/EtOAc = 10:1, v/v) to afford 2g as a white
solid (28.2 mg, 86%); mp: 150−152 °C. 1H NMR (400 MHz,
CDCl3): δ 1.17 (t, J = 7.6 Hz, 3 H), 2.55 (q, J = 7.6 Hz, 2 H), 6.50 (s,
1 H), 6.92 (s, 1 H), 7.03 (s, 4 H), 7.31−7.35 (m, 7 H), 7.45−7.47 (m,
3 H). 13C{H} NMR (100 MHz, CDCl3): δ 15.6, 28.2, 119.7, 123.1,
128.0, 128.1, 128.5, 128.9, 129.0, 129.1, 129.5, 135.2, 138.2, 140.2,
140.5, 150.2, 164.2. HRMS (ESI, m/z): calcd for C23H22NO: [M +
H]+ = 328.1696; found: 328.1690. IR (neat, cm−1): 3417, 2923, 1895,
1645, 1602, 1542, 1313, 1189, 1028, 908, 829, 744, 690, 614, 507, 453.
N-(4-Bromophenyl)-3,3-diphenylacrylamide (2h). The resultant
residue was purified by flash silica gel column chromatography
(eluent:petroleum ether/EtOAc = 10:1, v/v) to afford 2h as a white
solid (20.7 mg, 55%); mp: 190−192 °C. 1H NMR (400 MHz,
CDCl3): δ 6.49 (s, 1 H), 6.90 (s, 1 H), 7.00 (d, J = 8.8 Hz, 2 H), 7.28−
7.37 (m, 9 H), 7.48 (t, J = 3.2 Hz, 3 H). 13C{H} NMR (100 MHz,
CDCl3): δ 121.0, 122.7, 128.0, 128.5, 129.1, 129.4, 129.5, 131.8, 136.7,
138.0, 140.2, 150.9, 164.3. HRMS (ESI, m/z): calcd for C21H17BrNO:
[M + H]+ = 378.0488; found: 378.0482. IR (neat, cm−1): 3308, 2926,
2252, 1893, 1655, 1597, 1530, 1307, 1243, 1183, 1070, 1006, 908, 826,
736, 698, 652, 585, 508, 460.
N-(4-Chlorophenyl)-3,3-diphenylacrylamide (2i). The resultant
residue was purified by flash silica gel column chromatography
(eluent:petroleum ether/EtOAc = 10:1, v/v) to afford 2i as a white
solid (25.6 mg, 77%); mp: 190−192 °C. 1H NMR (400 MHz,
CDCl3): δ 6.49 (s, 1 H), 6.95 (s, 1 H), 7.05 (d, J = 8.8 Hz, 2 H), 7.50
(d, J = 8.8 Hz, 2 H), 7.29−7.37 (m, 7 H), 7.47−7.48 (m, 3 H). 13C{H}
NMR (100 MHz, CDCl3): δ 120.7, 122.7, 128.0, 128.5, 128.8, 129.0,
129.1, 129.4, 129.5, 136.2, 138.1, 140.2, 150.9, 164.3. HRMS (ESI, m/
z): calcd for C21H17ClNO: [M + H]+ = 334.0993; found: 334.0985. IR
(neat, cm−1): 3306, 2926, 2252, 1895, 1656, 1596, 1534, 1489, 1307,
1243, 1185, 1092, 908, 830, 736, 699, 511, 475, 409.
N-(3-Chlorophenyl)-3,3-diphenylacrylamide (2j). The resultant
residue was purified by flash silica gel column chromatography
(eluent:petroleum ether/EtOAc = 10:1, v/v) to afford 2j as a white
solid (29.3 mg, 88%); mp: 162−164 °C. 1H NMR (400 MHz,
CDCl3): δ 6.49 (s, 1 H), 6.88 (d, J = 8.0 Hz, 1 H), 6.99 (d, J = 8.0 Hz,
2 H), 7.10 (t, J = 8.0 Hz, 1 H), 7.29−7.37 (m, 8 H), 7.47−7.49 (m, 3
H). 13C{H} NMR (100 MHz, CDCl3): δ 117.4, 119.6, 122.5, 124.1,
128.1, 128.5, 129.1, 129.1, 129.4, 129.4, 129.7, 134.5, 138.0, 138.7,
140.2, 151.2, 164.3. HRMS (ESI, m/z): calcd for C21H17ClNO: [M +
H]+ = 334.0993; found: 334.0987. IR (neat, cm−1): 3423, 2924, 2123,
1961, 1806, 1651, 1481, 1408, 1265, 1183, 1097, 907, 867, 738, 700,
580, 547, 457.
N-(4-Fluorophenyl)-3,3-diphenylacrylamide (2k). The resultant
residue was purified by flash silica gel column chromatography
(eluent:petroleum ether/EtOAc = 10:1, v/v) to afford 2k as a white
solid (27.6 mg, 87%); mp: 134−136 °C. 1H NMR (400 MHz,
CDCl3): δ 6.50 (s, 1 H), 6.88 (t, J = 8.8 Hz, 2 H), 6.96 (s, 1 H), 7.05−
7.09 (m, 2 H), 7.29−7.36 (m, 7 H), 7.47 (t, J = 3.2 Hz, 3 H). 13C{H}
NMR (100 MHz, CDCl3): δ 115.4 (d, J = 22.0 Hz), 121.2 (d, J = 8.0
Hz), 121.3, 122.7, 128.0, 128.5, 129.0, 129.3, 129.5, 133.6, 138.1,
140.3, 150.7, 159.2 (d, J = 242.0 Hz), 164.3. HRMS (ESI, m/z): calcd
for C21H17FNO: [M + H]+ = 318.1280; found: 318.1289. IR (neat,
cm−1): 3290, 3059, 2925, 2251, 1956, 1891, 1810, 1657, 1508, 1405,
1310, 1212, 908, 836, 733, 696, 650, 578, 513, 450.
3,3-Diphenyl-N-(p-tolyl)acrylamide (2e). The resultant residue was
purified by flash silica gel column chromatography (eluent:petroleum
ether/EtOAc = 10:1, v/v) to afford 2e as a white solid (26.1 mg, 83%);
mp: 154−156 °C. 1H NMR (400 MHz, CDCl3): δ 2.25 (s, 3 H), 6.50
(s, 1 H), 6.90 (s, 1 H), 7.00 (s, 4 H), 7.30−7.35 (m, 7 H), 7.44−7.46
(m, 3 H). 13C{H} NMR (100 MHz, CDCl3): δ 20.8, 119.6, 123.2,
128.0, 128.5, 128.9, 129.0, 129.1, 129.3, 129.5, 133.7, 135.0, 138.2,
140.5, 150.2, 164.2. HRMS (ESI, m/z): calcd for C22H20NO: [M +
H]+ = 314.1539; found: 314.1535. IR (neat, cm−1): 3404, 3293, 3056,
2924, 2248, 1655, 1600, 1517, 1404, 1313, 1243, 1182, 1029, 908, 733,
698, 649, 512, 453.
N-(3-Fluorophenyl)-3,3-diphenylacrylamide (2l). The resultant
residue was purified by flash silica gel column chromatography
(eluent:petroleum ether/EtOAc = 10:1, v/v) to afford 2l as a white
solid (26.5 mg, 84%); mp: 130−132 °C. 1H NMR (400 MHz,
CDCl3): δ 6.49 (s, 1 H), 6.64−6.73 (m, 2 H), 7.02 (s, 1 H), 7.08−7.17
(m, 2 H), 7.29−7.37 (m, 7 H), 7.47−7.49 (m, 3 H). 13C{H} NMR
(100 MHz, CDCl3): δ 107.0 (d, J = 26.0 Hz), 110.7 (d, J = 22.0 Hz),
114.6, 122.6, 128.0, 128.3, 128.5, 129.1 (d, J = 4.0 Hz), 129.4 (d, J =
6.0 Hz), 129.8, 129.9, 138.0, 139.1 (d, J = 11.0 Hz), 140.2, 151.1, 162.8
(d, J = 243.0 Hz), 164.3. HRMS (ESI, m/z): calcd for C21H17FNO:
[M + H]+ = 318.1280; found: 318.1285. IR (neat, cm−1): 3404, 3263,
2923, 1954, 1806, 1656, 1601, 1489, 1262, 1202, 1076, 1030, 907, 867,
739, 697, 579, 549, 455.
3,3-Diphenyl-N-(m-tolyl)acrylamide (2f). The resultant residue
was purified by flash silica gel column chromatography (eluent:petro-
leum ether/EtOAc = 10:1, v/v) to afford 2f as a white solid (27.0 mg,
1
86%); mp: 142−144 °C. H NMR (400 MHz, CDCl3): δ 2.25 (s, 3
H), 6.49 (s, 1 H), 6.81−6.84 (m, 2 H), 6.94 (s, 1 H), 7.07 (t, J = 7.6
Hz, 2 H), 7.30−7.35 (m, 7 H), 7.45−7.47 (m, 3 H). 13C{H} NMR
(100 MHz, CDCl3): δ 21.4, 116.6, 120.2, 123.1, 124.9, 128.0, 128.4,
128.6, 128.9, 129.0, 129.2, 129.5, 137.5, 138.1, 138.7, 140.5, 150.4,
164.3. HRMS (ESI, m/z): calcd for C22H20NO: [M + H]+ = 314.1539;
found: 314.1535. IR (neat, cm−1): 3398, 3288, 2923, 2372, 1651, 1608,
1545, 1307, 1263, 1199, 1030, 908, 737, 696, 580, 555, 517, 456.
7622
dx.doi.org/10.1021/jo5013948 | J. Org. Chem. 2014, 79, 7616−7625