The Journal of Organic Chemistry
Page 12 of 16
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2-Methyl-N-phenyl-2-(p-tolyl)propanamide (2d): White solid, 35.5 mg, 56% yield. mp: 85.5-86.1 ºC. H
NMR (400 MHz, CDCl3): δ 7.36–7.32 (m, 4H), 7.27–7.17 (m, 4H), 7.04 (m, 1H), 6.84 (s, 1H), 2.36 (s,
3H),1.64 (s, 6H). 13C {1H} NMR (100 MHz, CDCl3): δ 175.8, 141.4, 137.9, 137.0, 129.6, 128.8, 126.4, 124.0,
119.5, 47.6, 27.0, 21.0. HRMS-ESI (m/z): Calculated for C17H20NO (M+H)+: 254.1545, Found: 254.1525.
2-Methyl-N-phenyl-2-(4-(trifluoromethyl)phenyl)propanamide (2e): White solid, 22.3 mg, 29% yield. mp:
117.5-119.6 ºC. 1H NMR (400 MHz, CDCl3): δ 7.66 (d, J = 8.0 Hz, 2H), 7.57 (d, J = 8.4 Hz, 2H), 7.38 (d, J =
8.0 Hz, 2H), 7.30 (d, J = 7.6 Hz, 2H), 6.74 (s, 1H). 1.69 (s, 6H). 13C {1H} NMR (100 MHz, CDCl3): 174.4,
148.8, 137.6, 129.6 (q, J = 32.4 Hz), 126.8, 125.9 (q, J = 3.7 Hz), 124.4, 123.9 (t, J = 136.1 Hz), 119.8, 48.1,
27.0. HRMS-ESI (m/z): Calculated for C17H17F3NO (M+H)+: 308.1262, Found: 308.1252.
2-(4-Methoxyphenyl)-2-methyl-N-phenylpropanamide (2f): Pale-yellow solid, 22.2 mg, 33% yield. mp:
83.2-84.5 ºC. 1H NMR (400 MHz, CDCl3): δ 7.39–7.33 (m, 4H), 7.29–7.22 (m, 2H), 7.07–7.03 (m, 1H), 6.98–
6.90 (m, 2H), 6.85 (s, 1H), 3.83 (s, 3H), 1.64 (s, 6H). 13C {1H} NMR (100 MHz, CDCl3): δ 175.9, 158.7, 137.9,
136.4, 128.8, 127.6, 124.0, 119.5, 114.2, 55.3, 47.3, 27.1. HRMS-ESI (m/z): Calculated for C17H20NO2 (M+H)+:
270.1494, Found: 270.1471.
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2-Methyl-N-phenyl-2-(o-tolyl)propanamide (2g): White solid, 62.7 mg, 99% yield. mp: 95.6-98.8 ºC. 1H
NMR (400 MHz, CDCl3): δ 7.51–7.49 (m, 1H), 7.36–7.34 (m, 2H), 7.32–7.18 (m, 6H), 7.11–7.03 (m, 1H),
6.85 (s, 1H), 2.31 (s, 3H), 1.66 (s, 6H). 13C {1H} NMR (100 MHz, CDCl3): δ 171.2, 138.8, 137.1, 134.6, 133.7,
132.4, 132.0, 131.7, 130.5, 129.1, 126.1, 58.4, 32.4, 20.8. HRMS-ESI (m/z): Calculated for C17H20NO (M+H)+:
254.1545, Found: 254.1543.
2-Methyl-N-phenyl-2-(m-tolyl)propanamide (2h): White solid, 45.2 mg, 76% yield. mp: 109.9-112.2 ºC 1H
NMR (400 MHz, CDCl3) δ 7.44–7.22 (m, 7H), 7.14 (d, J = 7.2 Hz, 1H), 7.06 (td, J = 7.2, 0.8 Hz, 1H), 6.83 (s,
1H), 2.39 (s, 3H), 1.66 (s, 6H). 13C {1H} NMR (100 MHz, CDCl3) δ 175.7, 144.4, 138.6, 138.0, 128.8, 128.1,
127.2, 124.0, 123.4, 119.6, 47.9, 27.0, 21.6. HRMS-ESI (m/z): Calculated for C17H20NO (M+H)+: 254.1545,
Found: 254.1540.
N,2-Diphenylpropanamide (2i):19 White solid, 19.0 mg, 34% yield. mp: 114.9-116.3 ºC. 1H NMR (400 MHz,
CDCl3): δ 7.47–7.21 (m, 1H), 7.17 (s, 1H), 7.06 (t, J = 7.2 Hz, 1H), 3.72 (q, J = 6.8 Hz, 1H), 1.69 (d, J = 7.2
Hz, 1H). 13C {1H} NMR (100 MHz, CDCl3): δ 175.6, 144.2, 137.0, 131.8, 129.1, 127.5, 126.4, 121.2, 116.6,
48.1, 26.9.
2,2-Difluoro-N,2-diphenylacetamide (2k):20 White solid, 16.1 mg, 26% yield. mp: 86.6-89.7 ºC. H NMR
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(400 MHz, CDCl3): δ 8.10 (s, 1H), 7.68 (d, J = 7.2 Hz, 2H), 7.58 (d, J = 7.6 Hz, 2H), 7.54–7.44 (m, 3H), 7.36
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