The Journal of Organic Chemistry
ARTICLE
1-Methyl-2-(4-methoxyphenyl)-4-phenyl-5-(4-trifluoro-
methylphenyl)-1H-imidazole (17b). Yield 80%, white solid, mp
192-193 °C, Rf = 0.45 (n-Hex/EtOAc = 1:1). IR (KBr) 3071, 2999,
2965, 2935, 2836, 1576, 1470, 1332, 1253 cm-1. 1H NMR (CDCl3) δ
3.51 (s, 3H), 3.88 (s, 3H), 7.04 (d, J = 8.8 Hz, 2H), 7.19-7.25 (m, 3H),
7.51 (d, J = 8.4 Hz, 2H), 7.54 (d, J = 7.8 Hz, 2H), 7.68 (d, J = 8.8 Hz, 2H),
7.73 (d, J = 8.4 Hz, 2H). 13C NMR (CDCl3) δ 33.3, 55.3, 114.1, 123.1,
124.1 (q, J = 272.1 Hz, CF3), 125.9 (q, J = 3.3 Hz, CdC-CF3), 126.7,
127.3, 128.3, 128.6, 130.1 (q, J = 32.3 Hz, C-CF3), 130.5, 131.1, 134.3,
135.1, 138.6, 148.8, 160.3. 19F NMR (CDCl3) δ -63.0. MS (EI) m/z:
408 (Mþ). HRMS (EI): exact mass calcd for C24H19F3N2O (Mþ);
408.1449. Found: 408.1457.
1-Methyl-2-(4-methoxyphenyl)-4-(4-trifluoromethylphe-
nyl)-5-phenyl-1H-imidazole (17c). Yield 84%, white solid, mp
196-197 °C, Rf = 0.45 (n-Hex/EtOAc = 1:1). IR (KBr) 2938, 2840,
1616, 1578, 1322, 1251 cm-1. 1H NMR (CDCl3) δ 3.49 (s, 3H), 3.88
(s, 3H), 7.04 (d, J = 8.8 Hz, 2H), 7.41-7.52 (m, 7H), 7.64-7.69
(m, 4H). 13C NMR (CDCl3) δ 33.0, 55.3, 114.1, 123.1, 124.5 (q, J =
272.1 Hz, CF3), 125.0 (q, J = 4.1 Hz, CdC-CF3), 126.7, 128.9 (q, J =
32.3 Hz, C-CF3), 129.0, 129.3, 130.5, 130.8, 130.9, 131.4, 136.1, 138.3,
148.3, 160.3. 19F NMR (CDCl3) δ -58.0. MS (EI) m/z: 408 (Mþ).
HRMS (EI): exact mass calcd for C24H19F3N2O (Mþ); 408.1449.
Found: 408.1459.
1-Methyl-2-(4-trifluoromethylphenyl)-4-(4-methoxyphe-
nyl)-5-phenyl-1H-imidazole (17d). Yield 97%, white solid, mp
162-165 °C, Rf = 0.60 (n-Hex/EtOAc = 1:1). IR (KBr) 2937, 2841,
1617, 1578, 1322, 1251 cm-1. 1H NMR (CDCl3) δ 3.54 (s, 3H), 3.77
(s, 3H), 6.79 (d, J = 9.0 Hz, 2H), 7.40-7.50 (m, 7H), 7.76 (d, J = 8.2 Hz,
2H), 7.90 (d, J = 8.2 Hz, 2H). 13C NMR (CDCl3) δ 33.2, 55.1, 113.6,
123.7 (q, J = 272.1 Hz, CF3), 125.5 (q, J = 3.3 Hz, CdC-CF3), 127.1,
128.1, 128.7, 129.1, 129.1, 130.4, 130.5 (q, J = 33.1 Hz, C-CF3), 130.9,
131.0, 134.5, 138.2, 146.2, 158.5. 19F NMR (CDCl3) δ -63.0. MS (EI)
m/z: 408 (Mþ). HRMS (EI): exact mass calcd for C24H19F3N2O (Mþ);
408.1449. Found: 408.1447.
130.3, 130.4, 130.6, 132.9, 135.5, 141.3, 145.8, 148.6. MS (EI) m/z: 355
(Mþ); HRMS (EI): calcd for C22H17N3O2 (Mþ); 355.1321. Found:
355.1334.
1-Methyl-2,5-diphenyl-4-(4-ethoxycarbonylphenyl)-1H-
imidazole (17h). Yield 56%, yellow solid, mp 122-122.5 °C, Rf =
0.25 (n-Hex/EtOAc = 1:1). IR (KBr) 3058, 2979, 1709, 1508, 1474,
1323, 1270, 1097, 859 cm-1. 1H NMR (CDCl3) δ 1.35 (t, J = 7.3 Hz,
3H), 3.50 (s, 3H), 4.34 (q, J = 7.3 Hz, 2H), 7.39-7.52 (m, 8H), 7.62
(d, J = 8.8 Hz, 2H), 7.74 (d, J = 6.8 Hz, 2H), 7.89 (d, J = 8.8 Hz, 2H).
13C NMR (CDCl3) δ 14.3, 33.1, 60.6, 126.1, 127.6, 128.3, 128.4,
128.7, 128.9, 128.9, 129.1, 130.4, 130.4, 130.5, 131.4, 136.4, 138.9,
147.9, 166.4. MS (EI) m/z: 382 (Mþ); HRMS (EI): calcd for
C25H22N2O2 (Mþ); 382.1681. Found: 382.1689.
1-Methyl-2,5-diphenyl-4-(4-N,N-dimethylaminophenyl)-
1H-imidazole (17i). Yield 84%, white solid, mp 144-145 °C, Rf =
0.13 (n-Hex/EtOAc = 4:1). IR (KBr) 3056, 2923, 2798, 1615, 1514,
1348, 1194 cm-1. 1H NMR (CDCl3) δ 2.84 (s, 6H), 3.43 (s, 3H), 6.55
(d, J = 8.8 Hz, 2H), 7.35-7.44 (m, 10 H), 7.68 (d, J = 7.3 Hz, 2H). 13C
NMR (CDCl3) δ 30.0, 40.5, 112.3, 127.8, 128.3, 128.5, 128.6, 128.8,
128.9, 128.9, 129.1, 129.3, 131.1, 131.7, 138.1, 147.5, 149.2. MS (EI) m/
z: 353 (Mþ); HRMS (EI): calcd for C24H23N3 (Mþ); 353.1892. Found:
353.1900.
1-Methyl-2,5-diphenyl-4-(3-methoxyphenyl)-1H-imida-
zole (17j). Yield 66%, colorless sticky oil, Rf = 0.25 (n-Hex/EtOAc =
1
1:1). IR (neat) 3056, 2932, 2832, 1601, 1238, 1043 cm-1. H NMR
(CDCl3) δ 3.51 (s, 3H), 3.66 (s. 3H), 6.73 (ddd, J = 7.8, 2.7, 1.5 Hz, 1H),
7.11-7.18 (m, 3H), 7.43-7.53 (m, 8H), 7.77 (d, J = 6.8 Hz, 2H). 13C
NMR (CDCl3) δ 33.0, 54.9, 114.5, 112.9, 119.4, 128.5, 128.6, 128.6,
128.8, 129.0, 129.1, 130.6, 130.8, 130.9, 131.2, 135.9, 137.5, 147.8, 159.4.
MS (EI) m/z: 340 (Mþ); HRMS (EI): calcd for C23H20N2O (Mþ);
340.1576. Found: 340.1570.
1-Methyl-2,5-diphenyl-4-(2-methylphenyl)-1H-imidazole
(17k). Yield 56%, white solid, mp 50-51 °C, Rf = 0.39 (n-Hex/EtOAc =
1
1:1). IR (KBr) 2921, 1601, 1498, 1469, 1377, 1073 cm-1. H NMR
(CDCl3) δ 2.21 (s, 3H), 3.72 (s, 3H), 7.12-7.18 (m, 2H), 7.30-7.55
(m, 10H), 7.83 (d, J = 7.3 Hz, 2H). 13C NMR (CDCl3) δ 20.3, 33.9,
125.2, 127.1, 127.4, 127.6, 128.4, 128.6, 128.9, 129.9, 130.1, 130.7, 130.8,
130.9, 131.5, 134.4, 137.0, 139.1, 147.8. MS (EI) m/z: 324 (Mþ);
HRMS (EI): calcd for C23H20N2 (Mþ); 324.1626. Found: 324.1624.
1-Methyl-2,5-diphenyl-4-(1-naphthyl)-1H-imidazole (17l).
Yield 78%, white solid, mp 95-96 °C, Rf = 0.25 (n-Hex/EtOAc= 4:1). IR
(KBr) 3053, 2952, 1470, 1374, 1314, 771, 698 cm-1. 1H NMR (CDCl3)
δ 3.72 (s, 3H), 7.26-7.52 (m, 12H), 7.74-7.84 (m, 4H), 8.30 (d, J = 8.8
Hz, 1H). 13C NMR (CDCl3) δ 34.0, 125.1, 125.4, 125.7, 126.7, 127.5,
127.8, 127.9, 128.4, 128.5, 128.5, 128.7, 129.0, 129.1, 130.1, 139.3, 130.9,
132.4, 132.6, 133.9, 138.1, 148.0. MS (EI) m/z: 360 (Mþ); HRMS (EI):
calcd for C26H20N2 (Mþ); 360.1626. Found: 360.1615.
1-Methyl-2-phenyl-4-(4-trifluoromethylphenyl)-5-(4-me-
thoxyphenyl)-1H-imidazole (17e). Yield 79%, white solid, mp
167-169 °C, Rf = 0.45 (n-Hex/EtOAc = 1:1). IR (KBr) 3070, 3009,
1
2962, 2938, 1616, 1562, 1322, 1251 cm-1. H NMR (CDCl3) δ 3.50
(s, 3H), 3.90 (s, 3H), 7.05 (d, J = 8.8 Hz, 2H), 7.34 (d, J =8.3 Hz, 2H),
7.44-7.53 (m, 5H), 7.70 (d, J = 8.3 Hz, 2H), 7.73 (d, J = 7.3 Hz, 2H).
13C NMR (CDCl3) δ 32.9, 55.3, 114.8, 122.8, 124.5 (q, J = 272.1 Hz,
CF3), 125.0 (q, J = 3.3 Hz, CdC-CF3), 126.0, 127.7 (q, J = 32.3 Hz,
C-CF3), 128.7, 129.0, 129.0, 130.8, 131.5, 132.1, 136.2, 138.4, 148.1,
160.2. 19F NMR (CDCl3) δ -62.6. MS (EI) m/z: 408 (Mþ). HRMS
(EI): exact mass calcd for C24H19F3N2O (Mþ); 408.1449. Found:
408.1442.
1-Methyl-2-(4-trifluoromethylphenyl)-4-phenyl-5-(4-me-
thoxyphenyl)-1H-imidazole (17f). Yield 92%, white solid, mp
146-147 °C, Rf = 0.45 (n-Hex/EtOAc = 1:1). IR (KBr) 3070, 3020,
2938, 2841, 2938, 2841, 1613, 1600, 1572, 1326, 1251 cm-1. 1H NMR
(CDCl3) δ 3.54 (s, 3H), 3.90 (s, 3H), 7.04 (d, J = 8.8 Hz, 2H), 7.18 (t, J =
7.3 Hz, 1H), 7.25 (t, J = 7.3 Hz, 2H), 7.35 (d, J = 8.8 Hz, 2H), 7.59 (d, J =
7.3 Hz, 2H), 7.77 (d, J = 8.3 Hz, 2H), 7.91 (d, J = 8.3 Hz, 2H). 13C NMR
(CDCl3) δ 33.1, 55.3, 114.6, 122.9, 124.1 (q, J = 272.1 Hz, CF3), 125.6
(q, J = 3.3 Hz, CdC-CF3), 126.5, 126.8, 128.2, 129.1, 130.3 (q, J = 32.3
Hz, C-CF3), 131.1, 132.1, 134.5, 134.6, 138.3, 146.1, 160.0. 19F NMR
(CDCl3) δ -63.0. MS (EI) m/z: 408 (Mþ). HRMS (EI): exact mass
calcd for C24H19F3N2O (Mþ); 408.1449. Found: 408.1442.
1-Methyl-2,5-bis(4-methoxyphenyl)-4-(4-trifluorometh-
ylphenyl)-1H-imidazole (17m). Yield 86%, white solid, mp 65-
66 °C, Rf = 0.43 (n-Hex/EtOAc = 1:1). IR (KBr) 2932, 1616, 1495,
1324, 1250 cm-1. 1H NMR (CDCl3) δ 3.46 (s, 3H), 3.87 (s, 3H), 3.88
(s, 3H), 7.01-7.04 (m, 4H), 7.31 (d, J = 8.8 Hz, 2H), 7.47 (d, J = 8.3 Hz,
2H), 7.65-7.69 (m, 4H). 13C NMR (CDCl3) δ 32.3, 54.9, 55.0, 113.8,
114.4, 122.5, 122.9, 124.2 (q, J = 271.3 Hz, CF3), 124.7 (q, J = 3.3 Hz,
CdC-CF3), 126.2, 127.7 (q, J = 32.3 Hz, C-CF3), 130.1, 130.9, 131.7,
135.6, 138.2, 147.7, 159.8, 159.9. 19F NMR (CDCl3) δ -62.6. MS (EI)
m/z: 438 (Mþ). HRMS (EI): exact mass calcd for C25H21F3N2O2
(Mþ); 438.1555. Found: 438.1553.
5-Phenylthiazole (18).32. Yield 53%, yellow solid, Rf = 0.22 (n-
Hex/EtOAc = 4:1). 1H NMR (CDCl3) δ 7.35-7.44 (m, 3H), 7.59 (d,
J = 9.3 Hz, 2H), 8.09 (s, 1H), 8.76 (s, 1H).
1-Methyl-2,5-diphenyl-4-(4-nitrophenyl)-1H-imidazole
(17g). Yield 75%, yellow solid, mp 207-209 °C, Rf = 0.20 (n-Hex/
EtOAc = 1:1). IR (KBr) 3057, 2950, 1594, 1558, 1508, 1382, 1321,
853 cm-1. 1H NMR (CDCl3) δ 3.50 (s, 3H), 7.40-7.54 (m, 8H), 7.69
(d, J = 8.8 Hz, 2H), 7.74 (d, J = 6.8 Hz, 2H), 8.05 (d, J = 8.8 Hz, 2H). 13C
NMR (CDCl3) δ 33.1, 123.5, 126.7, 128.7, 129.0, 129.2, 129.3, 129.4,
2-(4-Methoxyphenyl)-5-phenylthiazole (19)33 (Method I).
Yield 88%, white solid, Rf = 0.50 (n-Hex/EtOAc = 3:1).1H NMR
(CDCl3) δ 3.87 (s, 3H), 6.98 (d, J = 8.8 Hz, 2H), 7.32 (t, J = 7.3 Hz,
2691
dx.doi.org/10.1021/jo200067y |J. Org. Chem. 2011, 76, 2680–2693