H. Ghosh, R. Yella, J. Nath, B. K. Patel
FULL PAPER
1323, 1289, 1212, 1129, 1069, 821, 785, 761, 731, 695, 577,
502 cm–1.
H), 7.59 (d, J = 8.8 Hz, 2 H), 9.22 (s, 1 H) ppm. 13C NMR
(100 MHz, CDCl3, [D6]DMSO): δ = 55.5, 108.7, 114.3, 116.6,
120.4, 121.2, 123.9, 131.6, 142.6, 147.7, 155.5, 159.2 ppm. IR
Characterization of Compounds: Compounds 1a, 2a, 4a, 6a, 8a, 12a,
13a,[10] 11a,[12] 3a,[32] 5a, 7a, 9a,[33] 10a,[34] 1b,[17] 3b,[35] 4b,[21a] 6b,
8b, 6c,[16a] 7b,[36] 1c,[17] 6d, and 8d[32] are known compounds. The
new compounds were fully characterized.
(KBr): ν = 3154, 3043, 2838, 1681, 1590, 1580, 1554, 1505, 1484,
˜
1369, 1347, 1231, 1174, 1006, 1031, 967, 821, 742, 626, 600,
515 cm–1. C14H12N2O2 (240.26): calcd. C 69.99, H 5.03, N 11.66;
found C 70.08, H 5.09, N 11.57.
Spectral Data for Selected Compounds
N-Phenyl-2-(phenylimino)imidazolidine-1-carbothioamide (1e): M.p.
190–192 °C. 1H NMR (400 MHz, CDCl3, [D6]DMSO): δ = 3.46 (t,
J = 7.9 Hz, 2 H), 4.45 (t, J = 8.0 Hz, 2 H), 5.39 (s, 1 H), 7.02 (m,
2 H), 7.08 (t, J = 6.4 Hz, 1 H), 7.19 (t, J = 7.2 Hz, 1 H), 7.35 (m,
4 H), 7.61 (m, 2 H) ppm. 13C NMR (100 MHz, CDCl3, [D6]-
DMSO): δ = 38.4, 48.4, 122.6, 123.7, 124.4, 125.7, 128.6, 129.5,
N-(2-Chlorophenyl)-1H-benzo[d]imidazol-2-amine (2b): M.p. 152–
1
154 °C. H NMR (400 MHz, CDCl3, [D6]DMSO): δ = 6.70 (br. s,
1 H), 6.89 (t, J = 7.2 Hz, 1 H), 7.07 (m, 2 H), 7.25–7.38 (m, 4 H),
8.66 (d, J = 6.8 Hz, 1 H) ppm. 13C NMR (100 MHz, CDCl3, [D6]-
DMSO): δ = 112.6, 118.9, 120.5, 121.6, 127.5, 128.8, 136.4,
139.1, 146.5, 151.9, 178.8 ppm. IR (KBr): ν = 3290, 3061, 2900,
˜
150.2 ppm. IR (KBr): ν = 3056, 2926, 1625, 1600, 1557, 1461, 1448,
˜
1319, 1267, 1233, 1034, 738, 617 cm–1. C13H10ClN3 (243.70): calcd.
C 64.07, H 4.14, N 17.24; found C 64.11, H 4.19, N 17.18.
1662, 1620, 1574, 1591, 1480, 1426, 1404, 1378, 1323, 1289, 1212,
1129, 1069, 821, 785, 761, 731, 695, 577, 502 cm–1. C16H16N4S
(296.40): calcd. C 64.84, H 5.44, N 18.90, S 10.82; found C 64.78,
H 5.36, N 18.79, S 10.73.
N-(3-Chlorophenyl)-6-methyl-1H-benzo[d]imidazol-2-amine
(3bЈ):
M.p. 95–97 °C. 1H NMR (400 MHz, CDCl3, [D6]DMSO): δ = 2.41
(s, 3 H), 4.62 (br. s, 1 H), 6.92 (t, J = 8.0 Hz, 2 H), 7.21 (m, 3 H),
7.44 (m, 1 H), 7.62 (s, 1 H) ppm. 13C NMR (100 MHz, CDCl3,
[D6]DMSO): δ = 21.6, 112.5, 112.8, 116.4, 118.0, 121.8, 122.4,
2-(2-Chlorophenylimino)-N-(2-chlorophenyl)imidazolidine-1-carbo-
thioamide (2e): M.p. 147–149 °C. 1H NMR (400 MHz, CDCl3,
[D6]DMSO): δ = 3.48 (t, J = 8.0 Hz, 2 H), 4.42 (t, J = 8.4 Hz, 2
H), 6.24 (s, 1 H), 7.02 (m, 1 H), 7.15 (m, 2 H), 7.21–7.30 (m, 2 H),
7.39 (m, 2 H), 8.02 (m, 1 H) ppm. 13C NMR (100 MHz, CDCl3,
[D6]DMSO): δ = 38.1, 48.3, 123.6, 124.1, 126.2, 126.6, 127.3, 127.4,
127.8, 128.8, 129.1, 129.6, 136.3, 143.3, 151.2, 179.1 ppm. IR
130.2, 130.9, 134.4, 134.6, 136.1, 141.2, 150.1 ppm. IR (KBr): ν =
˜
2921, 1648, 1594, 1558, 1478, 1275, 1094, 912, 856, 798, 770, 678,
594 cm–1. C14H12ClN3 (257.72): calcd. C 65.25, H 4.69, N 16.30;
found C 65.11, H 4.73, N 16.22. MS (ESI): calcd. for C14H13N3Cl
[MH]+ 258.73; found 258.08.
(KBr): ν = 3230, 2889, 1689, 1600, 1581, 1556, 1470, 1415, 1395,
˜
1364, 1322, 1294, 1123, 1067, 1048, 779, 742, 684 cm– 1
.
N-(4-Methoxyphenyl)-6-methyl-1H-benzo[d]imidazol-2-amine (8bЈ):
M.p. 114–116 °C. 1H NMR (400 MHz, CDCl3, [D6]DMSO): δ =
2.42 (s, 3 H), 3.77 (s, 3 H), 4.80 (br. s, 1 H), 6.85 (d, J = 9.2 Hz, 2
H), 6.90 (d, J = 8.0 Hz, 1 H), 7.12 (s, 1 H), 7.20 (d, J = 8.0 Hz, 1
H), 7.40 (d, J = 8.8 Hz, 2 H) ppm. 13C NMR (100 MHz, CDCl3,
[D6]DMSO): δ = 21.5, 55.5, 112.0, 112.5, 114.5, 121.5, 121.9, 130.5,
C16H14Cl2N4S (365.28): calcd. C 52.61, H 3.86, N 15.34, S 8.78;
found C 52.66, H 3.83, N 15.29, S 8.73.
2-(3-Chlorophenylimino)-N-(2-chlorophenyl)imidazolidine-1-carbo-
thioamide (3e): M.p. 138–140 °C. 1H NMR (400 MHz, CDCl3,
[D6]DMSO): δ = 3.46 (t, J = 7.6 Hz, 2 H), 4.41 (t, J = 7.6 Hz, 2
H), 5.82 (s, 1 H), 6.92 (m, 1 H), 7.04–7.08 (m, 2 H), 7.14 (m, 1 H),
7.27 (m, 2 H), 7.47 (m, 1 H), 7.76 (m, 1 H) ppm. 13C NMR
(100 MHz, CDCl3, [D6]DMSO): δ = 38.3, 48.4, 121.2, 122.4, 122.9,
123.7, 124.1, 125.6, 129.5, 130.5, 133.9, 134.7, 140.2, 147.8, 152.1,
132.6, 134.4, 136.3, 151.9, 155.6 ppm. IR (KBr): ν = 3053, 2924,
˜
2850, 1663, 1573, 1509, 1458, 1405, 1276, 1239, 1178, 1031, 826,
800, 740, 652, 596, 519 cm–1. C15H15N3O (253.30): calcd. C 71.13,
H 5.97, N 16.59; found C 71.18, H 6.03, N 16.52.
178.6 ppm. IR (KBr): ν = 2894, 1667, 1586, 1560, 1474, 1403, 1376,
˜
1322, 1294, 1133, 1078, 898, 828, 791, 679, 581 cm–1. C16H14Cl2N4S
(365.28): calcd. C 52.61, H 3.86, N 15.34, S 8.78; found C 52.68,
H 3.87, N 15.28, S 8.74.
N-(2-Chlorophenyl)-1,3-benzoxazol-2-amine (2c): M.p. 109–111 °C.
1H NMR (400 MHz, CDCl3, [D6]DMSO): δ = 7.09 (m, 1 H), 7.22
(m, 1 H), 7.31 (m, 1 H), 7.43 (m, 3 H), 7.58 (d, J = 8.0 Hz, 1 H),
7.84 (s, 1 H), 8.57 (d, J = 8.4 Hz, 1 H) ppm. 13C NMR (100 MHz,
CDCl3, [D6]DMSO): δ = 109.1, 117.6, 119.4, 121.9, 122.3, 123.5,
2-(4-Bromophenylimino)-N-(4-bromophenyl)imidazolidine-1-carbo-
thioamide (6e): M.p. 180–182 °C. 1H NMR (400 MHz, CDCl3,
[D6]DMSO): δ = 3.47 (t, J = 7.6 Hz, 2 H), 4.44 (t, J = 8.4 Hz, 2
H), 4.78 (s, 1 H), 6.89 (d, J = 8.4 Hz, 2 H), 7.45 (m, 4 H), 7.52 (d,
J = 8.8 Hz, 2 H) ppm. 13C NMR (100 MHz, CDCl3, [D6]DMSO):
δ = 38.6, 48.7, 117.2, 119.0, 124.6, 126.1, 131.9, 132.9, 138.3, 145.6,
124.2, 127.9, 129.2, 134.5, 142.2, 147.6, 157.1 ppm. IR (KBr): ν =
˜
3230, 3029, 1661, 1589, 1571, 1531, 1458, 1339, 1317, 1245, 1229,
1166, 1055, 1003, 969, 920, 743, 707, 630, 494 cm–1. C13H9ClN2O
(244.68): calcd. C 63.82, H 3.71, N 11.45; found C 63.87, H 3.67,
N 11.37.
152.1, 178.9 ppm. IR (KBr): ν = 3230, 2813, 1658, 1589, 1572,
˜
N-(3-Chlorophenyl)-1,3-benzoxazol-2-amine (3c): M.p. 184–186 °C.
1H NMR (400 MHz, CDCl3, [D6]DMSO): δ = 6.99 (d, J = 8.0 Hz,
1 H), 7.12 (t, J = 7.6 Hz, 1 H), 7.22 (t, J = 7.6 Hz, 1 H), 7.28 (t, J
= 8.4 Hz, 1 H), 7.35 (d, J = 8.0 Hz, 1 H), 7.46 (d, J = 7.6 Hz, 1
H), 7.63 (d, J = 7.4 Hz, 1 H), 7.92 (s, 1 H), 10.35 (s, 1 H) ppm.
13C NMR (100 MHz, CDCl3, [D6]DMSO): δ = 108.2, 115.5, 116.4,
117.0, 121.2, 121.4, 123.4, 129.4, 133.6, 139.6, 141.8, 146.8,
1530, 1458, 1365, 1338, 1246, 1230, 1165, 1056, 1033, 1003, 970,
919, 836, 742, 710, 631 cm–1. C16H14Br2N4S (454.19): calcd. C
42.31, H 3.11, N 12.34, S 7.06; found C 42.35, H 3.08, N 12.27, S
7.00.
2-(p-Tolylimino)-N-(p-tolyl)imidazolidine-1-carbothioamide (7e):
M.p. 142–144 °C. 1H NMR (400 MHz, CDCl3, [D6]DMSO): δ =
2.32 (s, 3 H), 2.33 (s, 3 H), 3.43 (t, J = 8.0 Hz, 2 H), 4.42 (t, J =
7.6 Hz, 2 H), 5.34 (s, 1 H), 6.90 (d, J = 8.0 Hz, 2 H), 7.14 (m, 4
H), 7.45 (d, J = 8.4 Hz, 2 H) ppm. 13C NMR (100 MHz, CDCl3,
[D6]DMSO): δ = 20.8, 21.0, 38.4, 48.4, 122.4, 124.5, 129.1, 130.0,
157.3 ppm. IR (KBr): ν = 3022, 2920, 1687, 1600, 1579, 1461, 1483,
˜
1350, 1246, 1170, 1080, 882, 776, 737, 676 cm–1. C13H9ClN2O
(244.68): calcd. C 63.82, H 3.71, N 11.45; found C 63.85, H 3.76,
N 11.39.
133.0, 135.4, 136.6, 143.8, 152.0, 178.9 ppm. IR (KBr): ν = 3017,
˜
N-(4-Methoxyphenyl)-1,3-benzoxazol-2-amine (8c): M.p. 136– 2918, 2850, 1670, 1624, 1565, 1507, 1471, 1408, 1364, 1315, 1285,
138 °C. 1H NMR (400 MHz, CDCl3, [D6]DMSO): δ = 3.80 (s, 3
H), 6.90 (d, J = 8.8 Hz, 2 H), 7.06 (t, J = 7.6 Hz, 1 H), 7.18 (t, J
1262, 1127, 1076, 822, 807, 765, 690, 509 cm–1. C18H20N4S
(324.45): calcd. C 66.64, H 6.21, N 17.27, S 9.88; found C 66.69,
= 7.6 Hz, 1 H), 7.29 (d, J = 8.0 Hz, 1 H), 7.42 (d, J = 7.6 Hz, 1 H 6.25, N 17.19, S 9.83.
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Eur. J. Org. Chem. 2008, 6189–6196