10.1002/ejoc.201901602
European Journal of Organic Chemistry
FULL PAPER
1-ethyl-3-phenyl-1-(m-tolyl) urea (3ab) Following general procedure B,
3ab was obtained in 75% yield (38 mg, 0.2 mmol) as a white solid. M.p.:
53.6-54.5 °C. IR (KBr, cm-1): ν 3313, 3021, 2975, 2926, 1655, 1597, 1533,
1487, 1363, 1261, 1242, 840. 1H NMR (400 MHz, CDCl3) δ 7.54 – 7.47 (m,
1H), 7.44 – 7.40 (m, 2H), 7.36 (td, J = 8.9, 8.0, 2.1 Hz, 3H), 7.25 (d, J =
7.6 Hz, 2H), 7.12 (tt, J = 7.2, 1.4 Hz, 1H), 6.25 (s, 1H), 3.93 (q, J = 7.1 Hz,
2H), 2.55 (s, 3H), 1.31 (t, J = 7.1 Hz, 3H). 13C NMR (101 MHz, CDCl3) δ
154.1, 141.1, 140.6, 139.1, 130.1, 129.4, 129.1, 128.9, 125.9, 122.8, 119.3,
44.3, 21.5, 13.9. HRMS-EI (m/z) calcd. for (C16H18N2O) 254.1419, found
254.1421.
(s, 1H), 3.77 – 3.70 (m, 2H), 1.59 – 1.49 (m, 2H), 1.35 (q, J = 7.4 Hz, 2H),
0.90 (t, J = 7.3 Hz, 3H). 13C NMR (151 MHz, CDCl3) δ 154.3, 141.6, 139.1,
130.4, 128.9, 128.9, 128.3, 122.9, 119.3, 49.4, 30.8, 20.2, 14.0. HRMS-EI
(m/z) calcd. for (C17H20N2O) 268.1576, found 268.1577.
1-cyclohexyl-1,3-diphenylurea (3ai) Following general procedure B, 3ai
was obtained in 52% yield (31 mg, 0.2 mmol) as a white solid. M.p.: 78.9-
79.6 °C. IR (KBr, cm-1): ν 3305, 3028, 2995, 2946, 1612, 1572, 1530, 1462,
1393, 1195. 1H NMR (400 MHz, CDCl3) δ 7.56 – 7.41 (m, 3H), 7.27 – 7.23
(m, 3H), 7.23 – 7.17 (m, 3H), 6.95 (tt, J = 6.5, 2.0 Hz, 1H), 5.81 (s, 1H),
4.51 (tt, J = 12.1, 3.6 Hz, 1H), 1.98 – 1.86 (m, 2H), 1.74 (dt, J = 14.1, 3.3
Hz, 2H), 1.41 (qt, J = 13.5, 3.6 Hz, 2H), 1.06 (qd, J = 12.4, 3.7 Hz, 2H),
0.97 – 0.81 (m, 2H). 13C NMR (151 MHz, CDCl3) δ 154.2, 139.2, 138.0,
131.3, 130.0, 129.0, 128.9, 122.8, 119.3, 54.7, 32.4, 26.1, 25.6. HRMS-EI
(m/z) calcd. for (C19H22N2O) 294.1732, found 294.1731.
1-ethyl-3-phenyl-1-(p-tolyl) urea (3ac) Following general procedure B,
3ac was obtained in 68% yield (35 mg, 0.2 mmol) as a white solid. M.p.:
62.9-63.5 °C. IR (KBr, cm-1): ν 3325, 3032, 2987, 2945,1682, 1602, 1545,
1434, 1396, 1259, 870. 1H NMR (400 MHz, CDCl3) δ 7.31 – 7.26 (m, 4H),
7.24 – 7.21 (m, 2H), 7.19 (d, J = 8.1 Hz, 2H), 6.97 (tt, J = 7.2, 1.4 Hz, 1H),
6.10 (s, 1H), 3.77 (q, J = 7.1 Hz, 2H), 2.42 (s, 3H), 1.15 (t, J = 7.1 Hz, 3H).
13C NMR (101 MHz, CDCl3) δ 154.3, 139.2, 138.5, 138.4, 131.0, 128.9,
128.8, 122.8, 119.3, 44.3, 21.3, 13.9. HRMS-EI (m/z) calcd. for
(C16H18N2O) 254.1419, found 254.1421.
N-phenylindoline-1-carboxamide (3aj) Following general procedure B,
3aj was obtained in 58% yield (27 mg, 0.2 mmol) as a white solid. 1H NMR
(400 MHz, CDCl3) δ 7.89 (d, J = 8.0 Hz, 1H), 7.48 – 7.43 (m, 2H), 7.38 –
7.30 (m, 2H), 7.20 (t, J = 7.9 Hz, 2H), 7.12 – 7.05 (m, 1H), 7.00 – 6.91 (m,
1H), 6.48 (s, 1H), 4.10 (t, J = 8.5 Hz, 2H), 3.25 (t, J = 8.5 Hz, 2H). 13C NMR
(151 MHz, CDCl3) δ 152.4, 143.3, 138.4, 130.8, 129.2, 127.9, 124.9, 123.8,
122.6, 120.3, 115.1, 47.7, 29.8, 28.1. HRMS-EI (m/z) calcd. for
(C15H14N2O) 238.1106, found 238.1107.
1-methyl-1,3-diphenylurea (3ad)15 Following general procedure B, 3ad
was obtained in 80% yield (36 mg, 0.2 mmol) as a white solid. 1H NMR
(400 MHz, CDCl3) δ 7.53 – 7.45 (m, 2H), 7.42 – 7.37 (m, 1H), 7.34 (dt, J =
8.2, 1.2 Hz, 2H), 7.30 – 7.27 (m, 2H), 7.23 (dd, J = 8.7, 7.0 Hz, 2H), 6.99
(tt, J = 7.1, 1.5 Hz, 1H), 6.23 (s, 1H), 3.35 (s, 3H). 13C NMR (151 MHz,
CDCl3) δ 154.6, 143.1, 139.0, 130.5, 129.0, 128.0, 127.6, 123.1, 119.4,
29.9. HRMS-EI (m/z) calcd. for (C14H14N2O) 256.1106, found 256.1108.
1-methyl-3-phenyl-1-(m-tolyl) urea (3ae) Following general procedure B,
3ae was obtained in 80% yield (36 mg, 0.2 mmol) as a white solid. M.p.:
78.7-79.5 °C. IR (KBr, cm-1): ν 3343, 3051, 2996, 2890, 1655, 1599, 1533,
1438, 1321, 1260. 1H NMR (400 MHz, CDCl3) δ 7.36 (td, J = 7.5, 1.1 Hz,
1H), 7.30 – 7.26 (m, 2H), 7.23 (dd, J = 8.8, 7.0 Hz, 2H), 7.18 (ddq, J = 7.5,
1.8, 0.9 Hz, 1H), 7.16 – 7.11 (m, 2H), 6.98 (tt, J = 6.9, 1.4 Hz, 1H), 6.26 (s,
1H), 3.32 (s, 3H), 2.40 (s, 3H). 13C NMR (151 MHz, CDCl3) δ 154.6, 142.9,
140.7, 139.0, 130.2, 128.9, 128.8, 128.2, 124.5, 123.0, 119.4, 37.4, 21.5.
HRMS-EI (m/z) calcd. for (C15H16N2O) 240.1263, found 240.1262.
1-isopropyl-1,3-diphenylurea (3af) Following general procedure B, 3af
was obtained in 52% yield (27 mg, 0.2 mmol) as a white solid. 1H NMR
(400 MHz, CDCl3) δ 7.57 – 7.54 (m, 1H), 7.53 – 7.47 (m, 2H), 7.31 (d, J =
1.8 Hz, 1H), 7.30 – 7.27 (m, 2H), 7.26 (d, J = 1.4 Hz, 2H), 7.23 (d, J = 8.6
Hz, 1H), 7.04 – 6.96 (m, 1H), 5.87 (s, 1H), 4.99 (p, J = 6.8 Hz, 1H), 1.15
(d, J = 6.9 Hz, 6H). 13C NMR (151 MHz, CDCl3) δ 154.2, 139.1, 137.5,
131.3, 130.0, 129.0, 128.9, 122.8, 119.4, 46.7, 21.6. HRMS-EI (m/z) calcd.
for (C16H18N2O) 254.1419, found 254.1420.
N-fluoro-N-tosylbenzamide (4) Following general procedure B,
compound 4 was obtained in 92% yield (269.5 mg, 1 mmol) as a white
solid. M.p.: 94.5-95.8 °C. 1H NMR (400 MHz, CDCl3) δ 7.94 – 7.84 (m, 2H),
7.76 – 7.71 (m, 2H), 7.68 – 7.63 (m, 1H), 7.57 – 7.47 (m, 2H), 7.42 – 7.36
(m, 2H), 2.48 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 169.1 (d, J = 4.7 Hz),
147.4, 134.9, 131.2 (d, J = 2.1 Hz), 130.9 (d, J = 2.4 Hz), 130.3, 129.6,
128.6, 22.0. 19F NMR (376 MHz, CDCl3) δ -50.38. HRMS-EI (m/z) calcd.
for (C14H12FNO3S) 293.0522, found 293.0520.
N-fluoro-N-((4-nitrophenyl) sulfonyl) benzamide (5) Following general
procedure B, compound 5 was obtained in 85% yield (275.4 mg, 1 mmol)
as a white solid. M.p.: 129.5-130.9 °C. 1H NMR (400 MHz, CDCl3) δ 8.47
– 8.41 (m, 2H), 8.13 – 8.07 (m, 2H), 7.94 – 7.86 (m, 2H), 7.76 – 7.68 (m,
1H), 7.57 – 7.49 (m, 2H). 13C NMR (101 MHz, CDCl3) δ 168.4, 151.9, 138.8,
135.6, 131.2, 131.0 (d, J = 2.9 Hz), 130.2 (d, J = 1.9 Hz), 128.9, 124.7. 19
F
NMR (376 MHz, CDCl3) δ -47.50. HRMS-EI (m/z) calcd. for (C13H9FN2O5S)
324.0216, found 324.0218.
N-((4-chlorophenyl) sulfonyl)-N-fluorobenzamide (6) Following general
procedure B, compound 6 was obtained in 90% yield (281 mg, 1 mmol) as
a white solid. M.p.: 94.7-96.1 °C. 1H NMR (400 MHz, CDCl3) δ 7.88 (d, J =
7.7 Hz, 2H), 7.80 (d, J = 8.2 Hz, 2H), 7.69 (t, J = 7.7 Hz, 1H), 7.58 (d, J =
8.2 Hz, 2H), 7.52 (d, J = 7.7 Hz, 2H). 13C NMR (101 MHz, CDCl3) δ 168.8
(d, J = 4.7 Hz), 142.9, 135.2, 131.7, 131.0, 131.0, 130.9 (d, J = 2.6 Hz),
130.8 (d, J = 2.1 Hz), 130.1, 128.7. 19F NMR (376 MHz, CDCl3) δ -49.09.
HRMS-EI (m/z) calcd. for (C13H9ClFNO3S) 312.9976, found 312.9975.
N-(phenylsulfonyl) benzamide (7)17 1H NMR (400 MHz, CDCl3) δ 7.90 (s,
1H), 7.89 – 7.84 (m, 2H), 7.68 – 7.62 (m, 2H), 7.59 – 7.52 (m, 1H), 7.51 –
7.44 (m, 2H), 7.40 – 7.33 (m, 2H), 7.19 – 7.11 (m, 1H). 13C NMR (151 MHz,
CDCl3) δ 165.9, 138.0, 135.1, 132.0, 129.2, 128.9, 127.2, 124.7, 120.4.
HRMS-EI (m/z) calcd. for (C13H11NO3S) 261.0460, found 261.0461.
N-phenylbenzamide (8)18 1H NMR (400 MHz, CDCl3) δ 7.97 (s, 1H), 7.90
– 7.82 (m, 2H), 7.71 – 7.61 (m, 2H), 7.58 – 7.51 (m, 1H), 7.46 (dd, J = 8.3,
6.7 Hz, 2H), 7.36 (t, J = 7.9 Hz, 2H), 7.19 – 7.11 (m, 1H). 13C NMR (101
MHz, CDCl3) δ 165.9, 138.1, 135.2, 132.0, 129.3, 129.0, 127.2, 124.7,
120.3. HRMS-EI (m/z) calcd. for (C13H11NO) 197.0841, found 197.0839.
1-benzyl-1,3-diphenylurea (3ag)16 Following general procedure B, 3ag
was obtained in 58% yield (35 mg, 0.2 mmol) as a white solid. 1H NMR
(400 MHz, CDCl3) δ 7.40 (dd, J = 8.2, 6.4 Hz, 2H), 7.37 – 7.34 (m, 1H),
7.34 – 7.30 (m, 2H), 7.30 – 7.26 (m, 5H), 7.24 (d, J = 1.5 Hz, 2H), 7.19 –
7.15 (m, 2H), 7.00 (tt, J = 7.2, 1.3 Hz, 1H), 6.19 (s, 1H), 4.94 (s, 1H). 13C
NMR (151 MHz, CDCl3) δ 154.48, 141.30, 138.93, 138.34, 130.34, 128.96,
128.83, 128.66, 128.53, 128.38, 127.43, 123.12, 119.47, 53.59. HRMS-EI
(m/z) calcd. for (C20H18N2O) 302.1419, found 302.1421.
1-butyl-1,3-diphenylurea (3ah) Following general procedure B, 3ah was
obtained in 56% yield (30 mg, 0.2 mmol) as a white solid. M.p.: 64.9-
65.6 °C. IR (KBr, cm-1): ν 3294, 3056, 2958, 2926, 2857, 1652, 1595, 1522,
1493, 1439, 1378, 1239. 1H NMR (400 MHz, CDCl3) δ 7.53 – 7.46 (m, 2H),
7.44 – 7.37 (m, 1H), 7.34 – 7.30 (m, 2H), 7.28 (d, J = 1.7 Hz, 1H), 7.25 (d,
J = 1.4 Hz, 1H), 7.22 (dd, J = 8.7, 6.9 Hz, 2H), 7.03 – 6.93 (m, 1H), 6.09
This article is protected by copyright. All rights reserved.