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N-(2-chlorophenyl)-N-methylbenzamide (3ai). Light yellow
solid, m. p.: 65-67 °C; 65% yield. 1H NMR (600 MHz, CDCl3) δ
(ppm) 7.28-7.26 (m, 2H), 7.26-7.22 (m, 1H), 7.19-7.15 (m, 4H),
6.95 (d, J = 8.4 Hz, 2H), 3.45 (s, 3H). 13C NMR (150 MHz,
CDCl3) δ (ppm) 171.1, 142.2, 135.7, 132.2, 130.5, 130.4, 129.8,
128.8, 127.9, 127.7, 127.6, 36.9. HRMS (ESI) m/z: Calculated
for C14H13ClNO: 246.0680 [M+H]+, Found: 246.0688.
CDCl3) δ (ppm) 170.1, 143.2, 136.4, 129.4, 129.0, 128.6, 127.9,
ACCEPTED MANUSCRIPT
127.6, 126.6, 45.3, 12.9. HRMS (ESI) m/z: Calculated for
C15H16NO: 226.1226 [M+H]+, Found: 226.1232.
N, N-dioctylbenzamide (3aq). Yellow oily liquid; 28% yield.
1H NMR (600 MHz, CDCl3) δ (ppm) 7.39-7.36 (m, 3H), 7.34 (dd,
J = 7.8, 3.6 Hz, 2H), 3.47 (t, J = 7.8 Hz, 2H), 3.17 (t, J = 7.8 Hz,
2H), 1.65 (t, J = 7.8 Hz, 2H), 1.48 (t, J = 7.8 Hz, 2H), 1.39-1.21
(m, 12H), 1.21-1.04 (m, 8H), 0.97-0.80 (m, 6H). 13C NMR (150
MHz, CDCl3) δ (ppm) 171.6, 137.4, 128.9, 128.3, 126.4, 49.0,
44.7, 31.8, 31.4, 29.4, 29.2, 29.0(2C), 28.6, 27.5, 27.1, 26.5, 22.6,
22.6, 14.04(2C). HRMS (ESI) m/z: Calculated for C23H40NO:
346.3104 [M+H]+, Found: 346.3113.
N-(2-iodophenyl)-N-methylbenzamide (3aj). White solid, m. p.:
1
135-137 °C; 71% yield. H NMR (600 MHz, CDCl3) δ (ppm)
7.75 (d, J = 7.8 Hz, 1H), 7.34 (d, J = 7.8 Hz, 2H), 7.17 (q, J = 7.2
Hz, 2H), 7.11 (t, J = 7.8 Hz, 2H), 7.07 (d, J = 7.8 Hz,1H), 6.85 (t,
J = 7.8 Hz, 1H), 3.35 (s, 3H). 13C NMR (150 MHz, CDCl3) δ
(ppm) 170.7, 146.9, 140.1, 135.7, 130.1, 129.7, 129.3, 129.0
128.3, 127.6, 99.1, 37.5. HRMS (ESI) m/z: Calculated for
C14H13INO: 338.0036 [M+H]+, Found: 338.0025.
4-chloro-N-methyl-N-phenylbenzamide (3ba). Colorless liquid;
66% yield. H NMR (600 MHz, CDCl3) δ (ppm) 7.26-7.19 (m,
1
4H), 7.18-7.13 (m, 1H), 7.13-7.10 (m, 2H), 7.04-6.98 (m, 2H),
3.47 (s, 3H). 13C NMR (150 MHz, CDCl3) δ (ppm) 169.4, 144.6,
135.6, 134.3, 130.2, 129.3, 128.0, 126.8, 126.7, 38.4. HRMS
(ESI) m/z: Calculated for C14H13ClNO: 246.0680 [M+H]+, Found:
246.0672.
N-(2-methoxyphenyl)-N-methylbenzamide (3ak). White solid;
1
m. p.: 105-107 °C; 67% yield. H NMR (600 MHz, CDCl3) δ
(ppm) 7.28 (d, J = 7.2 Hz, 2H), 7.18-7.06 (m, 4H), 6.99 (d, J =
7.8 Hz, 1H), 6.81-6.72 (m, 2H), 3.69 (s, 3H), 3.34 (s, 3H). 13C
NMR (150 MHz, CDCl3) δ (ppm) 171.6, 163.4, 154.4, 136.4,
129.3, 129.1, 128.6, 127.8, 127.3, 120.7, 111.7, 55.2, 37.0.
HRMS (ESI) m/z: Calculated for C15H16NO2: 242.1176 [M+H]+,
Found: 242.1169.
4-iodo-N-methyl-N-phenylbenzamide (3ca). Light yellow solid;
m. p.: 91-93 °C; 73% yield. 1H NMR (600 MHz, CDCl3) δ (ppm)
7.50-7.46 (m, 2H), 7.26-7.19 (m, 2H), 7.18-7.13 (m, 1H), 7.04-
6.97 (m, 4H), 3.46 (s, 3H). 13C NMR (150 MHz, CDCl3) δ (ppm)
169.6, 144.6, 136.9, 130.4, 129.3, 126.8, 126.8, 122.3, 96.2, 38.4.
HRMS (ESI) m/z: Calculated for C14H13INO: 338.0036 [M+H]+,
Found: 338.0023.
N-(4-ethylphenyl)-N-methylbenzamide (3al). Yellow oily
liquid; 66% yield. 1H NMR (600 MHz, CDCl3) δ (ppm) 7.29 (d, J
= 7.2 Hz, 2H), 7.21 (t, J = 7.2 Hz, 1H), 7.14 (t, J = 7.8 Hz, 2H),
7.02 (d, J = 7.8 Hz, 2H), 6.93 (d, J = 7.8 Hz, 2H), 3.46 (s, 3H),
2.55 (q, J = 7.8 Hz, 2H), 1.16 (t, J = 7.8 Hz, 3H). 13C NMR (150
MHz, CDCl3) δ (ppm) 170.6, 142.5, 142.5, 136.1, 129.4, 128.7,
128.5, 127.6, 126.7, 38.4, 28.2, 15.3. HRMS (ESI) m/z:
Calculated for C16H18NO: 240.1383 [M+H]+, Found: 240.1389.
N-methyl-4-nitro-N-phenylbenzamide (3da). White solid, m. p.:
110-111 °C; 48% yield. H NMR (600 MHz, CDCl3) δ (ppm)
1
8.00 (d, J = 7.2 Hz, 2H), 7.43 (d, J = 8.4 Hz, 2H), 7.23 (t, J = 7.8
Hz, 2H), 7.17 (t, J = 7.8 Hz, 1H), 7.01 (d, J = 7.8 Hz, 2H), 3.50 (s,
3H). 13C NMR (150 MHz, CDCl3) δ (ppm) 168.3, 147.9, 143.8,
142.1, 129.5(4C), 127.3, 126.9, 123.0, 38.3. HRMS (ESI) m/z:
Calculated for C14H13N2O3: 257.0921 [M+H]+, Found: 257.0915.
N-(4-butylphenyl)-N-methylbenzamide (3am). Yellow oily
liquid; 53% yield. 1H NMR (600 MHz, CDCl3) δ (ppm) 7.28 (d, J
= 7.8 Hz, 2H), 7.22-7.18 (m, 1H), 7.13 (t, J = 7.8 Hz, 2H), 7.00
(d, J = 7.8 Hz, 2H), 6.91 (d, J = 7.8 Hz, 2H), 3.46 (s, 3H), 2.51 (t,
J = 7.8 Hz, 2H), 1.54-1.48 (m, 2H), 1.30-1.25 (m, 2H), 0.88 (t, J
= 7.8 Hz, 3H). 13C NMR (150 MHz, CDCl3) δ (ppm) 170.6,
142.4, 141.2, 136.1, 129.4, 129.0, 128.7, 127.6, 126.6, 38.4, 35.0,
33.3, 22.1, 13.8. HRMS (ESI) m/z: Calculated for C18H22NO:
268.1696 [M+H]+, Found: 268.1685.
3-chloro-N-methyl-N-phenylbenzamide (3ea). Yellow oil;
58% yield. H NMR (600 MHz, CDCl3) δ (ppm) 7.33 (t, J = 2.4
1
Hz, 1H), 7.23 (t, J = 7.8 Hz, 2H), 7.20-7.13 (m, 2H), 7.10-7.00
(m, 4H), 3.47 (s, 3H). 13C NMR (150 MHz, CDCl3) δ (ppm)
169.0, 144.4, 137.6, 133.8, 129.7, 129.3, 128.9, 128.9, 126.9,
126.9, 126.7, 38.4. HRMS (ESI) m/z: Calculated for C14H13ClNO:
246.0680 [M+H]+, Found: 246.0688.
N-methyl-N-(naphthalen-2-yl)benzamide (3an). White solid;
m. p.: 122-124 °C; 52% yield. H NMR (600 MHz, CDCl3) δ
3-methoxy-N-methyl-N-phenylbenzamide (3fa). Colorless
liquid; 61% yield. 1H NMR (600 MHz, CDCl3) δ (ppm) 7.21 (t, J
= 7.8 Hz, 2H), 7.14-7.09 (m, 1H), 7.04-7.01 (m, 3H), 6.86-6.81
(m, 2H), 6.75 (ddd, J = 7.8, 3.0, 1.2 Hz, 1H), 3.62 (s, 3H), 3.47 (s,
3H). 13C NMR (150 MHz, CDCl3) δ (ppm) 170.3, 158.9, 144.9,
137.1, 129.1, 128.7, 126.8, 126.5, 121.2, 116.0, 113.7, 55.1, 38.4.
HRMS (ESI) m/z: Calculated for C15H16NO2: 242.1176 [M+H]+,
Found: 242.1168.
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(ppm) 7.78-7.73 (m, 1H), 7.69 (d, J = 9.0 Hz, 2H), 7.49 (d, J =
2.4 Hz, 1H), 7.47-7.41 (m, 2H), 7.35 (d, J = 7.8 Hz, 2H), 7.19-
7.14 (m, 2H), 7.11 (t, J = 7.8 Hz, 2H), 3.58 (s, 3H). 13C NMR
(150 MHz, CDCl3) δ (ppm) 170.8, 142.4, 135.9, 133.4, 131.5,
129.6, 129.0, 128.7, 127.8, 127.6, 127.6, 126.6, 126.2, 125.3,
124.8, 38.6. HRMS (ESI) m/z: Calculated for C18H16NO:
262.1226 [M+H]+, Found: 262.1219.
N,3-dimethyl-N-phenylbenzamide (3ga). Yellow oily liquid;
59% yield. H NMR (600 MHz, CDCl3) δ (ppm) 7.22-7.17 (m,
N-methyl-N-(naphthalen-1-yl)benzamide (3ao). Light yellow
liquid; 55% yield. 1H NMR (600 MHz, CDCl3) δ (ppm) 8.03 (d, J
= 8.4 Hz, 1H), 7.85 (d, J = 7.8 Hz, 1H), 7.69 (d, J = 7.8 Hz, 1H),
7.61 (ddd, J = 8.4, 6.6, 1.2 Hz, 1H), 7.52 (ddd, J = 8.4, 7.2, 1.2
Hz, 1H), 7.26-7.22 (m, 4H), 7.11-7.06 (m, 2H), 6.98 (t, J = 7.8
Hz, 2H), 3.54 (s, 3H). 13C NMR (150 MHz, CDCl3) δ (ppm)
171.8, 141.2, 135.9, 134.5, 130.0, 129.6, 128.7, 128.7, 128.0,
127.7, 127.5, 127.3, 126.4, 125.5, 122.7, 38.4. HRMS (ESI) m/z:
Calculated for C18H16NO: 262.1226 [M+H]+, Found: 262.1233.
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3H), 7.13-7.10 (m, 1H), 7.04-7.00 (m, 3H), 7.00-6.97 (m, 2H),
3.47 (s, 3H), 2.20 (s, 3H). 13C NMR (151 MHz, CDCl3) δ (ppm)
170.8, 145.0, 137.5, 135.8, 130.3, 129.4, 129.0, 127.4, 126.8,
126.4, 125.7, 38.4, 21.2. HRMS (ESI) m/z: Calculated for
C15H16NO: 226.1226 [M+H]+, Found: 226.1222.
2-chloro-N-methyl-N-phenylbenzamide (3ha). Yellow oil;
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49% yield. H NMR (600 MHz, CDCl3) δ (ppm) 7.20-7.14 (m,
3H), 7.14-7.05 (m, 5H), 7.04 (t, J = 7.2 Hz, 1H), 3.50 (s, 3H). 13
C
N-ethyl-N-phenylbenzamide (3ap). Yellow oily liquid; 75%
yield. 1H NMR (600 MHz, CDCl3) δ (ppm) 7.29-7.26 (m, 2H),
7.21-7.16 (m, 3H), 7.14-7.09 (m, 3H), 7.02-6.99 (m, 2H), 3.97 (q,
J = 7.2 Hz, 2H), 1.21 (t, J = 7.2 Hz, 3H). 13C NMR (150 MHz,
NMR (150 MHz, CDCl3) δ (ppm) 168.1, 143.2, 136.5, 130.9,
129.7, 129.4, 128.9, 128.7, 127.2, 126.8, 126.1, 37.1. HRMS
(ESI) m/z: Calculated for C14H13ClNO: 246.0680 [M+H]+, Found:
246.0673.