The Journal of Organic Chemistry
Article
MHz, CDCl3): δ 28.1, 36.4, 39.3, 41.5, 119.9, 124.1, 128.9, 138.0,
176.1. HRMS-ESI (m/z): calcd for C17H22NO [M + H]+: 256.1696,
found 256.1700.
168.4. HRMS-ESI (m/z): calcd for C8H9ClNO [M + H]+: 170.0367,
found 170.0372.
N-(4-Bromophenyl)acetamide (3ja). Purification by column
chromatography (ethyl acetate/hexane = 1:5), brown red solid, mp
N-Phenylbenzamide (3aj). Purification by column chromatog-
raphy (ethyl acetate/hexane = 1:5), brown solid, mp 91−94 °C, 45%
yield (17.7 mg); 1H NMR (400 MHz, CDCl3): δ 7.15 (t, J = 7.42 Hz,
1H), 7.37 (t, J = 7.91 Hz, 2H), 7.47 (t, J = 7.45 Hz, 2H), 7.53−7.57
(m, 1H), 7.65 (d, J = 7.82 Hz, 2H), 7.85−7.87 (m, 2H), 7.91 (s, 1H);
13C{1H} NMR (100 MHz, CDCl3): δ 120.3, 124.6, 127.0, 128.8,
129.1, 131.8, 135.0, 138.0, 165.8. HRMS-ESI (m/z): calcd for
C13H12NO [M + H]+: 198.0913, found 198.0907.
1
147−150 °C, 45% yield (19.3 mg); H NMR (400 MHz, CDCl3): δ
2.17 (s, 3H), 7.32 (s, 1H), 7.39−7.44 (m, 4H); 13C NMR (100 MHz,
CDCl3): δ 24.6, 116.9, 121.4, 132.0, 136.9, 168.3. HRMS-ESI (m/z):
calcd for C8H7BrNO [M − H]−: 211.9717, found 211.9715.
N-(4-(Trifluoromethyl)phenyl)acetamide (3ka). Purification by
column chromatography (ethyl acetate/hexane = 1:5), white solid,
mp 147−149 °C, 58% yield (23.5 mg); 1H NMR (400 MHz, CDCl3):
δ 2.21 (s, 3H), 7.56 (d, J = 8.56 Hz, 2H), 7.64 (d,J = 8.24 Hz, 3H);
13C{1H} NMR (100 MHz, CDCl3): δ 24.7, 119.4, 124.1 (q, J =
269.85 Hz), 125.9, 126.3 (q, J = 3.74 Hz), 140.9, 168.7. HRMS-ESI
(m/z): calcd for C9H9F3NO [M + H]+: 204.0631, found 204.0638.
N-(Naphthalen-2-yl)acetamide (3la). Purification by column
chromatography (ethyl acetate/hexane = 1:5), brown solid, mp
N-(4-Methoxyphenyl)acetamide (3ba). Purification by column
chromatography (ethyl acetate/hexane = 1:5), light yellow solid, mp
1
120−122 °C, 78% yield (25.7 mg); H NMR (400 MHz, CDCl3): δ
2.15 (s, 3H), 3.78 (s, 3H), 6.83−6.87 (m, 2H), 7.27 (s, 1H), 7.37−
7.41 (m, 2H); 13C{1H} NMR (100 MHz, CDCl3): δ 24.3, 55.5,
114.1, 122.0, 131.0, 156.5, 168.3. HRMS-ESI (m/z): calcd for
C9H12NO2 [M + H]+: 166.0863, found 166.0866.
1
124−125 °C, 53% yield (19.6 mg); H NMR (500 MHz, CDCl3): δ
2.20 (s, 3H), 7.36−7.46 (m, 3H), 7.73−7.76 (m, 3H), 7.81 (s, 1H),
8.17 (s, 1H); 13C{1H} NMR (100 MHz, CDCl3): δ 24.6, 116.7,
120.0, 125.0, 126.5, 127.5, 127.6, 128.7, 130.6, 133.8, 135.4, 168.8.
HRMS-ESI (m/z): calcd for C12H12NO [M + H]+: 186.0913, found
186.0907.
N-(3-Methoxyphenyl)acetamide (3ca). Purification by column
chromatography (ethyl acetate/hexane = 1:5), red oil, 65% yield (21.5
mg); 1H NMR (400 MHz, CDCl3): δ 2.15 (s, 3H), 3.37 (s, 3H), 6.65
(dd, J = 8.20 Hz, J = 1.92 Hz, 1H), 6.98 (d, J = 7.40 Hz, 1H), 7.19 (t,
J = 8.12 Hz, 1H), 7.27 (s, 1H), 7.71 (s, 1H); 13C{1H} NMR (100
MHz, CDCl3): δ 24.6, 55.3, 105.8, 110.0, 112.1, 129.6, 139.2, 160.1,
168.7. HRMS-ESI (m/z): calcd for C9H12NO2 [M + H]+: 166.0863,
found 166.0868.
N-(Pyridin-2-yl)acetamide (3ma). Purification by column chro-
matography (ethyl acetate/hexane = 1:5), yellow oil, 57% yield (15.5
1
mg); H NMR (400 MHz, CDCl3): δ 2.22 (s, 3H), 7.03−7.06 (m,
1H), 7.70−7.74 (m, 1H), 8.23 (d, J = 8.44 Hz, 1H), 8.25−8.27 (m,
1H), 8.81 (s, 1H); 13C{1H} NMR (100 MHz, CDCl3): δ 24.7, 114.2,
119.7, 138.6, 147.4, 151.6, 168.9. HRMS-ESI (m/z): calcd for
C7H9N2O [M + H]+: 137.0709, found 137.0707.
N-(2-Methoxyphenyl)acetamide (3da). Purification by column
chromatography (ethyl acetate/hexane = 1:5), brown solid, 73% yield
1
(24.1 mg), mp 75−77 °C; H NMR (400 MHz, CDCl3): δ 2.20 (s,
3H), 3.87 (s, 3H), 6.87 (d, J = 7.92 Hz, 1H), 6.93−6.97 (m, 1H),
7.01−7.05 (m, 1H), 7.78 (s, 1H), 8.35 (d, J = 7.72 Hz, 1H); 13C{1H}
NMR (100 MHz, CDCl3): δ 24.9, 55.6, 109.9, 119.8, 121.1, 123.6,
127.7, 147.7, 168.2. HRMS-ES (m/z): calcd for C9H12NO2 [M +
H]+: 166.0863, found 166.0865.
N-(Thiophen-2-yl)acetamide (3na). Purification by column
chromatography (ethyl acetate/hexane = 1:5), black solid, mp 133−
1
135 °C, 51% yield (14.4 mg); H NMR (400 MHz, CDCl3): δ 2.20
(s, 3H), 6.65 (dd, J = 3.68 Hz, J = 1.36 Hz, 1H), 6.82−6.85 (m, 1H),
6.88 (dd, J = 5.52 Hz, J = 1.00 Hz, 1H), 8.27 (s, 1H); 13C{1H} NMR
(100 MHz, CDCl3): δ 23.3, 111.9, 118.1, 123.9, 138.9, 166.8. HRMS-
ESI (m/z): calcd for C6H8NOS [M + H]+: 142.0321, found
142.0316.
N-(p-Tolyl)acetamide (3ea). Purification by column chromatog-
raphy (ethyl acetate/hexane = 1:5), light yellow solid, mp 131−133
1
°C, 86% yield (25.6 mg); H NMR (400 MHz, CDCl3): δ 2.14 (s,
3H), 2.30 (s, 3H), 7.10 (d, J = 8.20 Hz, 2H), 7.37 (d, J = 8.48 Hz,
2H), 7.40−7.41 (m, 1H); 13C{1H} NMR (100 MHz, CDCl3): δ 20.9,
24.5, 120.1, 129.5, 133.9, 135.4, 168.4. HRMS-ESI (m/z): calcd for
C9H12NO [M + H]+: 150.0913, found 150.0918.
N-(m-Tolyl)acetamide (3fa). Purification by column chromatog-
raphy (ethyl acetate/hexane = 1:5), yellow oil, 70% yield (20.9 mg);
1H NMR (400 MHz, CDCl3): δ 2.15 (s, 3H), 2.31 (s, 3H), 6.91 (d, J
= 7.56 Hz, 1H), 7.16−7.20 (m, 1H), 7.26−7.35 (m, 2H), 7.55 (s,
1H); 13C{1H} NMR (100 MHz, CDCl3): δ 21.5, 24.5, 117.1, 120.6,
125.1, 128.8, 137.9, 138.9, 168.6. HRMS-ESI (m/z): calcd for
C9H12NO [M + H]+: 150.0913, found 150.0918.
3-Phenyl-N-propylpropanamide (3of). Purification by column
chromatography (ethyl acetate/hexane = 1:5), light yellow oil, 74%
yield (28.3 mg); 1H NMR (400 MHz, CDCl3): δ 0.84 (t, J = 7.42 Hz,
3H), 1.39−1.48 (m, 2H), 2.45−2.48 (m, 2H), 2.93−2.97 (m, 2H),
3.13−3.18 (m, 2H), 5.56 (s, 1H), 7.18−7.21 (m, 3H), 7.22−7.26 (m,
1H), 7.27−7.30 (m, 1H); 13C{1H} NMR (100 MHz, CDCl3): δ 11.3,
22.7, 31.8, 38.5, 41.3, 126.2, 128.3, 128.5, 140.9, 172.4. HRMS-ESI
(m/z): calcd for C12H18NO [M + H]+: 192.1383, found 192.1391.
N-Butyl-3-phenylpropanamide (3pf). Purification by column
chromatography (ethyl acetate/hexane = 1:5), light yellow oil, 84%
yield (34.4 mg); 1H NMR (400 MHz, CDCl3): δ 0.88 (t, J = 7.28 Hz,
3H), 1.20−1.29 (m, 2H), 1.36−1.43 (m, 2H), 2.44−2.48 (m, 2H),
2.94−2.98 (m, 2H), 3.17−3.22 (m, 2H), 5.42 (s, 1H), 7.18−7.23 (m,
3H), 7.27−7.30 (m, 2H); 13C{1H} NMR (100 MHz, CDCl3): δ 13.7,
20.0, 31.6, 31.8, 38.6, 39.3, 126.2, 128.4, 128.5, 140.9, 172.2. HRMS-
ESI (m/z): calcd for C13H20NO [M + H]+: 206.1539, found
206.1544.
N-Pentyl-3-phenylpropanamide (3qf). Purification by column
chromatography (ethyl acetate/hexane = 1:5), light yellow oil, 87%
yield (38.1 mg); 1H NMR (400 MHz, CDCl3): δ 0.87 (t, J = 7.18 Hz,
3H), 1.17−1.24 (m, 2H), 1.26−1.31 (m, 2H), 1.37−1.45 (m, 2H),
2.44−2.48 (m, 2H), 2.94−2.98 (m, 2H), 3.16−3.21 (m, 2H), 5.40 (s,
1H), 7.18−7.21 (m, 3H), 7.27−7.30 (m, 2H); 13C{1H} NMR (100
MHz, CDCl3): δ 14.0, 22.3, 29.0, 19.2, 31.8, 38.6, 39.5, 126.3, 128.4,
128.5, 140.9, 172.1. HRMS-ESI (m/z): calcd for C14H22NO [M +
H]+: 220.1696, found 220.1701.
N-(3,4-Dimethylphenyl)acetamide (3ga). Purification by column
chromatography (ethyl acetate/hexane = 1:5), light yellow solid, mp
1
84−86 °C, 74% yield (24.1 mg); H NMR (400 MHz, CDCl3): δ
2.13 (s, 3H), 2.20 (d, J = 2.88 Hz, 6H), 7.04 (d, J = 8.04 Hz, 1H),
7.21 (d, J = 7.92 Hz, 1H), 7.27 (s, 1H), 7.59 (s, 1H); 13C{1H} NMR
(100 MHz, CDCl3): δ 19.2, 19.9, 24.4, 117.6, 121.5, 129.9, 132.6,
135.7, 137.1, 168.5. HRMS-ESI (m/z): calcd for C10H14NO [M +
H]+: 164.1070, found 164.1076.
N-(4-Fluorophenyl)acetamide (3ha). Purification by column
chromatography (ethyl acetate/hexane = 1:5), brown red solid, mp
1
141−144 °C, 56% yield (17.1 mg); H NMR (400 MHz, CDCl3): δ
2.16 (s, 3H), 6.97−7.01 (m, 2H), 7.45 (s, 2H), 7.59 (s, 1H); 13C{1H}
NMR (100 MHz, CDCl3): δ 24.4, 115.6 (d, J = 22.35 Hz), 121.8 (d, J
= 7.82 Hz), 133.8 (d, J = 2.87 Hz), 159.4 (d, J = 241.96 Hz), 168.3.
HRMS-ESI (m/z): calcd for C8H9FNO [M + H]+: 154.0663, found
154.0665.
N-Heptadecyl-3-phenylpropanamide (3rf). Purification by col-
umn chromatography (ethyl acetate/hexane = 1:5), white solid, mp
N-(4-Chlorophenyl)acetamide (3ia). Purification by column
chromatography (ethyl acetate/hexane = 1:5), light yellow solid,
mp 156−157 °C, 52% yield (17.6 mg); 1H NMR (400 MHz, CDCl3):
δ 2.17 (s, 3H), 7.26−7.28 (m, 2H), 7.45 (d, J = 8.27 Hz, 3H);
13C{1H} NMR (100 MHz, CDCl3): δ 24.6, 121.1, 129.0, 129.3, 136.4,
1
56−58 °C, 71% yield (55.0 mg); H NMR (400 MHz, CDCl3): δ
0.86−0.90 (m, 3H), 1.26−1.33 (m, 28H), 1.36−1.43 (m, 2H), 2.44−
2.48 (m, 2H), 2.94−2.99 (m, 2H), 3.16−3.21 (m, 2H), 5.38 (s, 1H),
7.19−7.20 (m, 3H), 7.27−7.31 (m, 2H); 13C{1H} NMR (100 MHz,
2824
J. Org. Chem. 2021, 86, 2820−2826