Paper
Organic & Biomolecular Chemistry
7.6 Hz, 2H), 3.09 (t, J = 7.6 Hz, 2H), 7.31 (dd, J1 = 2.0 Hz, J2 = 126.7, 127.5, 130.4, 131.0, 135.2, 135.3, 135.4, 154.1, 166.4;
8.4 Hz, 1H), 7.73 (d, J = 8.4 Hz, 1H), 7.94 (d, J = 2.0 Hz, 1H); FTIR (KBr): 756, 1268, 1429, 1464, 1638 cm−1; HRMS (m/z):
13C{1H} NMR (100 MHz, CDCl3) δ 14.2, 22.6, 28.9, 29.7, 31.6, [M + H]+ calculated for C13H9ClNS: 246.0144; found: 246.0153.
34.6, 122.3, 122.5, 125.2, 132.0, 133.5, 154.3, 174.6; FTIR (KBr):
754, 904, 1267, 1431, 1517, 2955, 3055 cm−1; HRMS (m/z):
5-Chloro-2-phenylbenzo[d]thiazole (3s)
[M
254.0777.
+
H]+ calculated for C13H17ClNS: 254.0770; found:
92 mg, 75% yield; orange solid; mp 138–140 °C [139–141 °C,
lit];26 Rf = 0.34 (2% ethyl acetate in hexanes); 1H NMR
(400 MHz, CDCl3) δ 7.34–7.38 (m, 1H), 7.48–7.53 (m, 3H), 7.80
(d, J = 8.8 Hz, 1H), 8.04–8.10 (m, 3H); 13C{1H} NMR (100 MHz,
CDCl3) δ 122.4, 123.2, 125.8, 127.8, 129.2, 131.4, 132.4, 133.4,
135.5, 155.1, 170.1; FTIR (KBr): 755, 1153, 1268, 1427, 1548,
3056 cm−1; HRMS (m/z): [M + H]+ calculated for C13H9ClNS:
246.0144; found: 246.0145.
5-Chloro-2-nonylbenzo[d]thiazole (3n)
112 mg, 76% yield; pale yellow liquid; Rf = 0.32 (2% ethyl
acetate in hexanes); 1H NMR (400 MHz, CDCl3) δ 0.87 (t, J =
6.4 Hz, 3H), 1.22–1.37 (m, 10H), 1.38–1.47 (m, 2H), 1.86 (quin,
J = 7.2 Hz, 2H), 3.09 (t, J = 7.6 Hz, 2H), 7.31 (dd, J1 = 1.6 Hz,
J2 = 8.4 Hz, 1H), 7.73 (d, J = 8.4 Hz, 1H), 7.94 (d, J = 2.0 Hz,
1H); 13C{1H} NMR (100 MHz, CDCl3) δ 14.2, 22.8, 29.2, 29.3,
29.4, 29.5, 29.8, 32.0, 34.6, 122.3, 122.6, 125.2, 132.0, 133.5,
154.3, 174.7; FTIR (KBr): 749, 903, 1266, 1431, 1551, 2929,
3055 cm−1; HRMS (m/z): [M + H]+ calculated for C16H23ClNS:
296.1239; found: 296.1243.
5-Chloro-2-(4-chlorophenyl)benzo[d]thiazole (3t)
94 mg, 67% yield; light yellow solid; mp 144–146 °C
1
[140–142 °C, lit];25 Rf = 0.44 (2% ethyl acetate in hexanes); H
NMR (400 MHz, CDCl3) δ 7.35 (d, J = 8.8 Hz, 1H), 7.42–7.48 (m,
2H), 7.75–7.80 (m, 1H), 7.95–8.00 (m, 2H), 8.02 (s, 1H); 13C{1H}
NMR (100 MHz, CDCl3) δ 122.4, 123.2, 126.0, 128.9, 129.5,
131.9, 132.6, 133.4, 137.6, 155.0, 168.6; FTIR (KBr): 753, 898,
1267, 1429, 1466, 2984, 3056 cm−1; HRMS (m/z): [M + H]+ cal-
culated for C13H8Cl2NS: 279.9754; found: 279.9757.
2-(tert-Butyl)-5-chlorobenzo[d]thiazole (3o)
77 mg, 68% yield; pale yellow liquid; Rf = 0.44 (2% ethyl
acetate in hexanes); H NMR (400 MHz, CDCl3) δ 1.51 (s, 9H),
1
7.28–7.33 (m, 1H), 7.74 (d, J = 8.8 Hz, 1H), 7.97 (d, J = 1.6 Hz,
1H); 13C{1H} NMR (100 MHz, CDCl3) δ 30.8, 38.6, 122.3, 122.7,
125.1, 131.9, 133.4, 154.3, 184.1; FTIR (KBr): 752, 1077, 1267,
1365, 1429, 1509, 2972, 3053 cm−1; HRMS (m/z): [M + H]+ cal-
culated for C11H13ClNS: 226.0457; found: 226.0461.
5-Chloro-2-(3-chlorophenyl)benzo[d]thiazole (3u)
99 mg, 71% yield; light yellow solid; mp 142–144 °C
1
[141–143 °C, lit];25 Rf = 0.44 (2% ethyl acetate in hexanes); H
NMR (400 MHz, CDCl3) δ 7.37–7.43 (m, 1H), 7.42–7.51 (m, 2H),
7.81 (d, J = 8.4 Hz, 1H), 7.94 (d, J = 7.2 Hz, 1H), 8.06–8.11 (m,
2H); 13C{1H} NMR (100 MHz, CDCl3) δ 122.5, 123.4, 125.9,
126.2, 127.6, 130.5, 131.4, 132.7, 133.4, 135.0, 135.4, 154.9,
2-Phenylbenzo[d]thiazole (3p)
86 mg, 81% yield; light yellow solid; mp 108–110 °C
[110–112 °C, lit];25 Rf = 0.25 (2% ethyl acetate in hexanes); H
1
168.2; FTIR (KBr): 755, 1268, 1426, 1514, 1638, 3057 cm−1
;
NMR (400 MHz, CDCl3) δ 7.39 (t, J = 8.0 Hz, 1H), 7.47–7.54 (m,
4H), 7.91 (d, J = 8.0 Hz, 1H), 8.06–8.14 (m, 3H); 13C{1H} NMR
(100 MHz, CDCl3) δ 121.8, 123.4, 125.3, 126.5, 127.7, 129.2,
131.1, 133.7, 135.2, 154.3, 168.2; FTIR (KBr): 958, 1156, 1268,
1309, 1442, 1506, 3012 cm−1; HRMS (m/z): [M + H]+ calculated
for C13H10NS: 212.0534; found: 212.0528.
HRMS (m/z): [M + H]+ calculated for C13H8Cl2NS: 279.9754;
found: 279.9755.
2-(2-Methoxyphenyl)benzo[d]thiazole (3v)
75 mg, 62% yield; white solid; mp 114–116 °C [120–121 °C,
lit];27 Rf = 0.24 (2% ethyl acetate in hexanes); 1H NMR
(400 MHz, CDCl3) δ 4.06 (s, 3H), 7.07 (d, J = 8.4 Hz, 1H), 7.14
(t, J = 7.6 Hz, 1H), 7.37 (t, J = 7.6 Hz, 1H), 7.43–7.53 (m, 2H),
7.93 (d, J = 7.6 Hz, 1H), 8.10 (d, J = 8.4 Hz, 1H), 8.54 (d, J = 8.0
Hz, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 55.9, 111.8, 121.3,
121.4, 122.4, 122.9, 124.7, 126.0, 129.7, 131.9, 136.2, 152.3,
157.4, 163.3; FTIR (KBr): 755, 1167, 1248, 1311, 1459, 1591,
2959, 3060 cm−1; HRMS (m/z): [M + H]+ calculated for
C14H12NOS: 242.0640; found: 242.0638.
2-(4-Chlorophenyl)benzo[d]thiazole (3q)
93 mg, 76% yield; light yellow solid; mp 108–110 °C [112 °C,
lit];26 Rf = 0.42 (2% ethyl acetate in hexanes); 1H NMR
(400 MHz, CDCl3) δ 7.40 (t, J = 7.6 Hz, 1H), 7.44–7.53 (m, 3H),
7.90 (d, J = 8.0 Hz, 1H), 8.00–8.05 (m, 2H), 8.06 (d, J = 8.4 Hz,
1H); 13C{1H} NMR (100 MHz, CDCl3) δ 121.8, 123.4, 125.6,
126.6, 128.8, 129.4, 132.2, 135.2, 137.2, 154.2, 166.8; FTIR
(KBr): 756, 1166, 1253, 1310, 1469, 1507, 3055 cm−1; HRMS
(m/z): [M + H]+ calculated for C13H9ClNS: 246.0144; found:
246.0145.
2-Benzylbenzo[d]thiazole (3w)
88 mg, 78% yield; pale yellow liquid; Rf = 0.13 (2% ethyl
acetate in hexanes); H NMR (400 MHz, CDCl3) δ 4.45 (s, 2H),
2-(3-Chlorophenyl)benzo[d]thiazole (3r)
1
95 mg, 77% yield; light yellow solid; mp 92–94 °C [97–99 °C, 7.27–7.33 (m, 1H), 7.34 (m, 1H), 7.35–7.41 (m, 4H), 7.46 (t, J =
lit];26 Rf = 0.28 (2% ethyl acetate in hexanes); 1H NMR 7.6 Hz, 1H), 7.79 (d, J = 8.0 Hz, 1H), 8.01 (d, J = 8.4 Hz, 1H);
(400 MHz, CDCl3) δ 7.38–7.48 (m, 3H), 7.48–7.54 (m, 1H), 13C{1H} NMR (100 MHz, CDCl3) δ 40.7, 121.6, 122.9, 124.9,
7.88–7.97 (m, 2H), 8.09 (d, J = 8.0 Hz, 1H), 8.11–8.14 (m, 1H); 126.0, 127.4, 129.0, 129.3, 135.8, 137.3, 153.4, 171.3; FTIR
13C{1H} NMR (100 MHz, CDCl3) δ 121.8, 123.6, 125.7, 125.8, (KBr): 754, 896, 1267, 1430, 1507, 2983, 3057 cm−1; HRMS
9750 | Org. Biomol. Chem., 2019, 17, 9743–9756
This journal is © The Royal Society of Chemistry 2019