Organic & Biomolecular Chemistry
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2H), 7.33–7.29 (m, 2H), 7.25–7.21 (m, 3H), 7.19 (d, J = 8.0 Hz, 130.2, 128.9, 128.8, 126.8, 125.5, 122.9, 41.4, 35.7; HRMS Calcd
2H), 6.24 (brs, 1H), 3.70 (q, J = 6.4 Hz, 2H), 2.92 (t, J = 6.4 Hz, for C15H15BrNO (M + H+): 304.0332; Found: 304.0334.
2H), 2.37 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 167.6, 141.9,
N-Phenethyl-4-nitrobenzamide (11a). Yellow solid. Mp:
139.1, 131.8, 129.3, 128.9, 128.8, 126.9, 126.7, 41.2, 35.8, 21.5; 148.1–150.7 °C; 1H NMR (400 MHz, CDCl3) δ 8.25 (d, J = 8.4
HRMS Calcd for C16H18NO (M + H+): 240.1383; Found: Hz, 2H), 7.84 (d, J = 8.4 Hz, 2H), 7.36–7.32 (m, 2H), 7.26–7.23
240.1384.
(m, 3H), 6.29 (brs, 1H), 3.75 (q, J = 6.8 Hz, 2H), 2.96 (t, J = 6.8
N-Benzyl-4-methylbenzamide (4b). Yellow solid. Mp: Hz, 2H); 13C NMR (100 MHz, CDCl3) δ 165.7, 149.7, 140.3,
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95.2–98.1 °C; H NMR (400 MHz, CDCl3) δ 7.61 (d, J = 6.8 Hz, 138.6, 129.0, 128.9, 128.2, 127.0, 124.0, 41.5, 35.6; HRMS Calcd
2H), 7.25 (brs, 5H), 7.13 (d, J = 6.8 Hz, 2H), 6.45 (brs, 1H), 4.54 for C15H15N2O3 (M + H+): 271.1077; Found: 271.1079.
(d, J = 4.8 Hz, 2H), 2.30 (s, 3H); 13C NMR (100 MHz, CDCl3)
N-Benzyl-4-nitrobenzamide
(11b). Yellow
solid.
Mp:
δ 167.4, 142.1, 138.4, 131.6, 129.3, 128.8, 128.0, 127.6, 127.1, 115.2–118.5 °C; 1H NMR (400 MHz, CDCl3) δ 8.23 (d, J = 7.6
44.2, 21.6; HRMS Calcd for C15H16NO (M + H+): 226.1226; Hz, 2H), 7.93 (d, J = 7.6 Hz, 2H), 7.34 (brs, 5H), 6.78 (brs, 1H),
Found: 226.1227
4.63 (d, J = 4.8 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ 165.5,
N-Octyl-4-methylbenzamide
(4c). Yellow
solid.
Mp: 149.7, 140.0, 137.5, 129.0, 128.3, 128.0, 123.9, 44.5; HRMS
115.5–117.9 °C; 1H NMR (400 MHz, CDCl3) δ 7.66 (d, J = 8.0 Calcd for C14H13N2O3 (M + H+): 257.0921; Found: 257.0924.
Hz, 2H), 7.22 (d, J = 8.0 Hz, 2H), 6.11 (brs, 1H), 6.25 (brs, 1H),
N-(Furan-2-ylmethyl)-4-nitrobenzamide (11c). Yellow solid.
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3.44 (q, J = 6.8 Hz, 2H), 2.39 (s, 3H), 1.64–1.57 (m, 2H), Mp: 135.2–136.5 °C; H NMR (400 MHz, CDCl3) δ 8.28 (d, J =
1.39–1.27 (m, 10H), 0.88 (t, J = 6.8 Hz, 3H); 13C NMR 8.8 Hz, 2H), 7.33–7.95 (d, J = 8.8 Hz, 2H), 7.39 (s, 1H), 6.55
(100 MHz, CDCl3) δ 167.7, 141.8, 132.1, 129.3, 129.2, 127.0, (brs, 1H), 6.37–6.33 (m, 2H), 4.67 (d, J = 5.6 Hz, 2H); 13C NMR
40.2, 31.9, 29.8, 29.4, 29.3, 27.1, 22.8, 21.5, 14.2; HRMS Calcd (100 MHz, CDCl3) δ 165.3, 150.5, 149.8, 142.8, 139.8, 128.4,
for C16H26NO (M + H+): 248.2009; Found: 248.2007.
N-Benzyl-4-methoxybenzamide (5a). White solid. Mp: H+): 247.0713; Found: 247.0717.
146.6–148.8 °C; 1H NMR (400 MHz, CDCl3) δ 7.78–7.74 (m,
N-Butyl-4-nitrobenzamide
124.0, 110.8, 108.4, 37.4; HRMS Calcd for C12H11N2O4 (M +
(11d). Yellow
solid.
Mp:
2H), 7.35–7.29 (m, 5H), 6.93–6.89 (m, 2H), 6.40 (brs, 1H), 4.63 131.4–133.6 °C; 1H NMR (400 MHz, CDCl3) δ 8.24 (d, J = 8.8
(d, J = 5.6 Hz, 2H), 3.84 (s, 3H); 13C NMR (100 MHz, CDCl3) Hz, 2H), 7.75 (d, J = 8.8 Hz, 2H), 7.55 (brs, 1H), 3.32 (q, J = 6.8
δ 167.1, 162.3, 138.5, 128.9, 128.8, 127.9, 127.6, 126.7, 113.8, Hz, 2H), 1.59–1.50 (m, 2H), 1.42–1.33 (m, 2H), 0.93 (t, J = 7.2
55.5, 44.1; HRMS Calcd for C15H16NO2 (M + H+): 242.1176; Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 160.0, 148.1, 138.6,
Found: 242.1179.
N-Phenethyl-4-fluorobenzamide (6a). Yellow solid. Mp: C11H15N2O3 (M + H+): 223.1077; Found: 223.1078.
134.2–136.6 °C; 1H NMR (400 MHz, CDCl3) δ 7.72–7.68 (m,
N-Octyl-4-nitrobenzamide (11e). Yellow solid.
127.7, 124.1, 39.6, 31.3, 20.1, 13.8; HRMS Calcd for
Mp:
2H), 7.33–7.29 (m, 2H), 7.25–7.20 (m, 3H), 7.07–7.03 (m, 2H), 136.2–138.5 °C; 1H NMR (400 MHz, CDCl3) δ 8.27 (d, J = 8.4
6.35 (brs, 1H), 3.69 (q, J = 6.8 Hz, 2H), 2.92 (t, J = 6.8 Hz, 2H); Hz, 2H), 7.94 (d, J = 8.4 Hz, 2H), 6.45 (brs, 1H), 3.47 (q, J = 6.8
13C NMR (100 MHz, CDCl3) δ 166.7, 166.0, 163.5, 138.9, 129.3, Hz, 2H), 1.68–1.60 (m, 2H), 1.38–1.27 (m, 10H), 0.90–0.83 (m,
129.2, 128.9, 128.8, 128.7, 126.9, 126.7, 115.7, 115.5, 41.4, 35.7; 3H); 13C NMR (100 MHz, CDCl3) δ 165.7, 149.6, 140.5, 128.2,
HRMS Calcd for C15H15FNO (M + H+): 244.1132; Found: 123.9, 40.6, 31.9, 29.6, 29.4, 29.3, 27.1, 22.7, 14.2; HRMS Calcd
244.1135.
for C15H23N2O3 (M + H+): 279.1703; Found: 279.1705.
N-Phenethyl-4-chlorobenzamide (7a). Yellow solid. Mp:
N-Isobutyl-4-nitrobenzamide (11f). Yellow solid. Mp:
114.4–117.1 °C; 1H NMR (400 MHz, CDCl3) δ 7.62 (d, J = 8.8 125.1–127.6 °C; 1H NMR (400 MHz, CDCl3) δ 8.28 (d, J = 8.8
Hz, 2H), 7.34 (d, J = 8.4 Hz, 2H), 7.30 (d, J = 7.6 Hz, 2H), 7.22 Hz, 2H), 7.94 (d, J = 8.8 Hz, 2H), 6.39 (brs, 1H), 3.32 (t, J = 6.4
(t, J = 7.6 Hz, 3H), 6.33 (brs, 1H), 3.68 (q, J = 6.8 Hz, 2H), 2.91 Hz, 2H), 1.97–1.90 (m, 1H), 1.00 (d, J = 6.4 Hz, 6H); 13C NMR
(t, J = 6.8 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ 166.6, 138.9, (100 MHz, CDCl3) δ 165.9, 149.6, 140.6, 128.2, 123.9, 47.8,
137.7, 133.1, 131.5, 128.9, 128.8, 128.4, 126.7, 41.3, 35.7; 28.7, 20.3; HRMS Calcd for C11H15N2O3 (M + H+): 223.1077;
HRMS Calcd for C15H15ClNO (M + H+): 260.0837; Found: Found: 223.1075.
260.0839.
N-(sec-Butyl)-4-nitrobenzamide (11g). Yellow solid. Mp:
N-Phenethyl-4-bromobenzamide (8a). Yellow solid. Mp: 114.4–117.1 °C; 1H NMR (400 MHz, CDCl3) δ 8.28 (d, J = 8.4
132.4–133.8 °C; 1H NMR (400 MHz, CDCl3) δ 7.61–7.47 (m, Hz, 2H), 7.92 (d, J = 8.4 Hz, 2H), 6.02 (d, J = 5.2 Hz, 1H),
4H), 7.35–7.31 (m, 2H), 7.27–7.22 (m, 3H), 6.14 (brs, 1H), 3.71 4.20–4.09 (m, 1H), 1.65–1.58 (m, 2H), 1.27 (d, J = 6.4 Hz, 3H),
(q, J = 6.8 Hz, 2H), 2.93 (t, J = 6.8 Hz, 2H); 13C NMR (100 MHz, 0.99 (t, J = 7.6 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 165.1,
CDCl3) δ 166.7, 138.9, 133.5, 131.9, 128.9, 128.8, 128.6, 126.8, 149.6, 140.7, 128.2, 123.9, 47.9, 29.8, 20.5, 10.6; HRMS Calcd
126.2, 41.3, 35.7; HRMS Calcd for C15H15BrNO (M + H+): for C11H15N2O3 (M + H+): 223.1077; Found: 223.1079.
304.0332; Found: 304.0334.
N-(1-Phenylethyl)-4-nitro benzamide (11h). Yellow solid.
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N-Phenethyl-3-bromobenzamide (9a). Yellow solid. Mp: Mp: 151.2–153.6 °C; H NMR (400 MHz, CDCl3) δ 8.19 (d, J =
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143.2–145.1 °C; H NMR (400 MHz, CDCl3) δ 7.84 (s, 1H), 7.59 8.8 Hz, 2H), 7.89 (d, J = 8.8 Hz, 2H), 7.38–7.32 (m, 4H),
(d, J = 8.0 Hz, 2H), 7.34–7.30 (m, 2H), 7.25–7.21 (m, 4H), 6.33 7.30–7.27 (m, 1H), 6.80 (d, J = 7.6 Hz, 1H), 5.34–5.27 (m, 1H),
(brs, 1H), 3.69 (q, J = 6.4 Hz, 2H), 2.92 (t, J = 6.8 Hz, 2H); 13C 1.61 (d, J = 7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 164.8,
NMR (100 MHz, CDCl3) δ 166.2, 138.8, 136.7, 134.5, 130.3, 149.6, 142.6, 140.2, 128.9, 128.3, 127.8, 126.3, 123.8, 49.9, 21.7;
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