4-Bromophenyl-phenylsulfide (3j)17. General procedure was
followed (8 h), colourless oil, 104 mg (0.39 mmol, 78% yield),
Rf (hexane) = 0.70; 1H NMR (CDCl3; 250 MHz): d 7.31–7.15 (m,
7H), 7.05 (d, J = 8.5 Hz, 2H); 13C NMR (CDCl3, 62.5 MHz):
d 135.4, 134.7, 132.1, 132.0, 131.5, 129.3, 127.5, 120.8; MS (EI,
70 eV) m/z (% relative intensity, ion): 266 (65, [M+]), 184(100),
152(32), 108(27), 92(26), 51(26).
(0.29 mmol, 58% yield), mp.: 98–99 ◦C, Rf (hexane : EtOAc 8 : 2) =
0.53; H NMR (CDCl3; 250 MHz): d 8.50 (d, J = 4.7 Hz, 1H),
1
8.27 (s, 1H), 8.50 (d, J = 8.7 Hz, 1H), 8.20 (d, J = 8.8 Hz, 1H),
7.63 (dd, J1 = 8.8 Hz, J2 = 1.8 Hz, 1H), 7.37 (d, J = 8.2 Hz, 2H),
7.20 (d, J = 8.1 Hz, 2H), 6.67 (d, J = 4.9 Hz, 1H); 13C NMR
(CDCl3, 62.5 MHz): d 150.5, 150.2, 146.5, 135.6, 131.8, 131.2,
131.0, 127.6(q), 127.3, 126.0, 124.7, 121.9(q), 121.6, 118.6, 21.3;
MS (EI, 70 eV) m/z (% relative intensity, ion): 319 (100, [M+]),
304(48), 207(18), 169(25), 91(32), 65(18). IR (ATR) 1326, 1284,
1162, 1148, 1120, 1066, 936, 806, 675 cm-1, HRMS calcd for
C17H13F3NS [M+H]+ 320.0715, found 320.0716.
3-(2,6-Dimethylphenylthio)-benzonitrile (3k). General proce-
dure was followed (8 h), white solid, 114 mg (0.48 mmol, 95%
yield); mp.: 77–78 ◦C, Rf (hexane : EtOAc 10 : 1) = 0.59; 1H NMR
(CDCl3; 250 MHz): d 7.26–7.04 (m, 6H), 6.98 (s, 1H), 2.3 (s, 6H);
13C NMR (CDCl3, 62.5 MHz): d 143.7, 140.4, 130.0, 129.5, 129.3,
128.7, 128.4, 128.0, 118.4, 113.0, 21.6; MS (EI, 70 eV) m/z (%
relative intensity, ion): 239(100, [M+]), 206(25), 190(18), 136(38),
105(41), 77(54). IR (ATR) 2225, 1561, 1460, 1399, 1378, 1194, 874,
798, 776, 681 cm-1, HRMS calcd for C15H14NS [M+H]+ 240.0841,
found 240.0843.
4-(4-Aminolphenylthio)-7-(trifluoromethyl)-quinoline
(3q).
General procedure was followed (24 h), yellow solid, 139 mg
(0.43 mmol, 87% yield), mp.: 137–138 ◦C, Rf (hexane : EtOAc
1 : 1) = 0.53; 1H NMR (CDCl3; 250 MHz): d 8.58 (d, J = 4.9 Hz,
1H), 8.35 (s, 1H), 8.27 (d, J = 8.7 Hz, 1H), 7.70 (dd, J1 = 8.7 Hz,
J2 = 1.7 Hz, 1H), 7.33 (d, J = 8.7 Hz, 2H), 6.77–6.71 (m, 3H),
4.15(s, 2H); 13C NMR (CDCl3, 62.5 MHz): d 151.8, 150.4, 148.7,
146.3, 137.5, 131.6, 131.0, 127.4(q), 127.1, 126.0, 124.6, 121.7(q),
117.9, 116.2, 114.1; MS (EI, 70 eV) m/z (% relative intensity,
ion): 320 (100, [M+]), 207(22), 169(22), 124(68), 80(41), IR (ATR)
1560, 1332, 1304, 1222, 1196, 1146, 1116, 826, 664 cm-1, HRMS
calcd for C16H12F3N2S [M+H]+ 321.0668, found: 321.0664
4-(2,6-Dimethylphenylthio)-benzophenone (3l). General proce-
dure was followed (8 h),◦slightly yellow solid, 108 mg (0.42 mmol,
1
84% yield), mp.: 91–92 C, Rf (hexane : EtOAc 8 : 2) = 0.65; H
NMR (CDCl3; 250 MHz): d 7.66 (dt, J1 = 8.7 Hz, J2 = 2.0 Hz, 2H),
7.21–7.08 (m, 3H), 6.85 (dt, J1 = 8.7 Hz, J2 = 2.0 Hz, 2H), 2.41 (s,
3H), 2.30 (s, 6H); 13C NMR (CDCl3, 62.5 MHz): d 196.9, 145.2,
143.8, 133.4, 129.8, 128.82, 128.76, 128.6, 124.6, 26.2, 21.6; MS
(EI, 70 eV) m/z (% relative intensity, ion): 256 (59, [M+]), 241(100),
198(27), 77(26). IR (ATR) 1676, 1584, 1355, 1259, 1106, 959, 819,
782, 620, 588 cm-1, HRMS calcd for C16H17OS [M+H]+ 257.0995,
found 257.0993.
4-(2-pyridylthio)-7-(trifluoromethyl)-quinoline (3r). General
procedure was followed◦(24 h), yellow solid, 53 mg (0.17 mmol,
1
69% yield), mp.: 57–58 C, Rf (hexane : EtOAc 1 : 1) = 0.40; H
NMR (CDCl3; 250 MHz): d 8.80 (d, J = 4.6 Hz, 1H), 8.44 (dd, J1 =
4.9 Hz, J1 = 0.9 Hz, 1H) 8.36 (s, 1H), 8.27 (d, J = 8.8 Hz, 1H), 7.64
(dd, J1 = 8.8 Hz, J2 = 1.6 Hz, 1H), 7.57–7.48 (m, 2H), 7.19–7.09
(m, 2H); 13C NMR (CDCl3, 62.5 MHz): d 155.6, 150.9, 150.6,
147.3, 143.1, 137.5, 132.0, 131.5, 129.4, 127.8(q), 126.2, 125.6,
125.4, 122.7(q), 122.2, 121.5; IR (ATR) 1574, 1557, 1453, 1416,
1326, 1286, 1193, 1111, 1066, 934, 831, 761, 680 cm-1, HRMS
calcd for C15H10F3N2S [M+H]+ 307.0511, found: 307.0511.
Dodecyl-phenylsulfide (3m)4h. General procedure was followed
(8 h), whit◦e solid, 60 mg (0.22 mmol, 43% yield); mp.: 31–32 ◦C,
lit.: 33–34 C, Rf (hexane) = 0.45; 1H NMR (CDCl3; 250 MHz): d
7.26–7.16 (m, 4H), 7.11–7.05 (m, 1H), 2.83 (t, J = 7.4 Hz, 2H), 1.57
(m, 2H), 1.18 (m, 18H), 0.81 (t, J = 6.4 Hz, 3H); 13C NMR (CDCl3,
62.5 MHz): d 137.0, 128.75, 128.74, 33.5, 31.9, 29.69, 29.63, 29.57,
29.49, 29.33, 29.15, 29.11, 28.8, 22.7, 14.1; MS (EI, 70 eV) m/z (%
relative intensity, ion): 278 (13, [M+]), 123(21), 110(100), 55(16).
2-(4-Aminolphenylthio)-4-(trifluoromethyl)-pyrimidine
(3s).
2-Phenylthio-pyridine (3n)14. General procedure was followed
(8 h), colourless oil, 86 mg (0.46 mmol, 92% yield from the reaction
of 2-iodopyridine and thiophenol), 55 mg (0.29 mmol, 59% yield
from the reaction of 2-iodopyridine and thiophenol), Rf (hexane :
EtOAc 8 : 2) = 0.54; 1H NMR (CDCl3; 250 MHz): d 8.41 (dd, J1 =
4.9 Hz, J2 = 0.9 Hz, 1H), 7.62–7.54 (m, 2H), 7.45–7.37 (m, 4H),
6.99–6.94 (m, 1H), 6.86 (d, J = 8.1 Hz, 1H); 13C NMR (CDCl3,
62.5 MHz): d161.3, 149.4, 136.6, 134.8, 130.8, 129.5, 129.0, 121.2,
119.7; MS (EI, 70 eV) m/z (% relative intensity, ion): 187 (28,
[M+]), 186(100) 78(13), 51(23).
General procedure was followed (24 h), yellow solid, 84 mg
(0.31 mmol, 62% yield), mp.: 109–111 ◦C, Rf (hexane : EtOAc
1 : 1) = 0.65; 1H NMR (CDCl3; 250 MHz): d 8.57 (d, J = 4.9 Hz,
1H), 7.27 (d, J = 8.4 Hz, 1H), 7.13 (d, J = 5.1 Hz, 1H), 6.61 (d,
J = 8.4 Hz, 1H), 3.69 (s, 1H); 13C NMR (CDCl3, 62.5 MHz): d
175.5, 159.6, 156.0, 155.4, 148.1, 136.9, 122.6, 117.9, 115.5, 115.4,
111.88, 111.84; MS (EI, 70 eV) m/z (% relative intensity, ion):
271 (100, [M+]), 202(32), 124(90), 80(57), IR (ATR) 1568, 1496,
1325, 1284, 1165, 1119, 1067, 811, 676 cm-1, HRMS calcd for
C11H9F3N3S [M+H]+ 272.0464, found: 272.0466.
3-Phenylthio-pyridine (3o)16. General procedure was followed
(8 h), slightly yellow oil, 88 mg (0.47 mmol, 94% yield), Rf (hexane
: EtOAc 6 : 4) = 0.57; 1H NMR (CDCl3; 250 MHz): d 8.55 (s, 1H),
8.45 (d, J = 4.58 Hz, 1H), 7.59 (dt, J1 = 7.9 Hz, J2 = 1.6 Hz), 7.40–
7.28 (m, 5H), 7.23–7.18 (m, 1H); 13C NMR (CDCl3, 62.5 MHz):
d 150.8, 147.7, 137.9, 133.8, 133.7, 131.7, 129.5, 127.8, 123.8; MS
(EI, 70 eV) m/z (% relative intensity, ion): 187 (100, [M+]), 115(15),
51(32).
2-(2-Pyridylthio)-4-(trifluoromethyl)-pyrimidine (3t). General
procedure was followed (24 h), yellow oil, 54 mg (0.20 mmol, 80%
1
yield), Rf (hexane : EtOAc 1 : 1) = 0.54; H NMR (CDCl3; 250
MHz): d 8,67 (d, J = 4.9 Hz, 1H), 8,58 (d, J = 4.8 Hz, 1H), 7.75–
7.71 (m, 2H), 7.30–7.24 (m, 2H); 13C NMR (CDCl3, 62.5 MHz): d
173.0, 159.8, 156.2, 155.7, 152.1, 150.3, 137.4, 129.9, 123.5, 122.1,
117.8, 112.80, 112.76; MS (EI, 70 eV) m/z (% relative intensity,
ion): 257 (69, [M+]), 199(52), 78(100), 51(59). IR (ATR) 1559,
1330, 1209, 1146, 1116, 833, 764, 732, 664 cm-1, HRMS calcd for
C10H7F3N3S [M+H]+ 258.0307, found: 258.0305
4-(4-Methylphenylthio)-7-(trifluoromethyl)-quinoline
(3p).
General procedure was followed (16 h), yellow solid, 92 mg
This journal is
The Royal Society of Chemistry 2011
Org. Biomol. Chem., 2011, 9, 711–716 | 715
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