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Naresh Kumar Katari et al.
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in dry DMF (10–15 mL) in 50 mL rb flask connected
to a reflux condensor was refluxed for 2 h. Progress
of the reaction was monitored by TLC. The reaction
mixture was filtered through celite. The filtrate was
concentrated in vacuo and the resulting mixture chro-
matographed on silica gel (DCM:MeOH) to yield
N-aryl-2−aminobenzazoles.
3443, 3077, 1626, 1574, 1210; H NMR (400 MHz,
DMSO-d6): δ 10.49 (br s, 1H, NH), 7.80–7.78 (m, 3H),
7.57 (d, J = 7.88 Hz, 1H), 7.31 (t, J = 7.56 Hz, 1H),
7.22–7.12 (m, 3H); Mass (ESI): 245.0 [M+H]+.
2.2g Benzooxazol-2-yl-(4-methoxy-phenyl)-amine (table 1,
Entry 7): solid; M.p.: 137–139◦C; IR (KBr, cm−1):
3383, 3043, 2836, 1674, 1579, 1510, 1232, 1031;
1H NMR (400 MHz, DMSO-d6): δ 10.60 (br s, 1H,
NH), 7.50 (d, J = 8.60 Hz, 1H), 7.30–7.10 (m,
4H), 6.91–6.78 (m, 3H), 3.85 (s, 3H); Mass (ESI):
241.0 [M+H]+.
2.2 Experimental data
2.2a Benzooxazol-2-yl-phenyl-amine (table 1, Entry 1):
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Light brown solid; M.p.: 142–143◦C; H NMR (400
MHz, DMSO-d6): δ 10.60 (br s, 1H, NH), 7.75 (d, J =
7.76 MHz, 2H), 7.44 (t, J = 7.96 Hz, 2H), 7.38–7.32
(m, 2H), 7.21 (t, J = 7.47 Hz, 1H), 7.12 (t, J = 7.62
Hz, 1H), 7.03 (t, J = 7.32 Hz, 1H); Mass (ESI): 211.0
[M+H]+.
2.2h Benzothiazol-2-yl-(4-methoxy-phenyl)-amine (table 1,
Entry 8): solid; M.p.: 166–167◦C; IR (KBr, cm−1):
3451, 3184, 2902, 1619, 1567, 1510, 1455, 1251,
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1030; H NMR (400 MHz, DMSO-d6): δ 10.25 (br
s, 1H, NH), 7.75 (d, J
=
7.64 Hz, 1H), 7.66
(d, J = 8.6 Hz, 2H), 7.53 (d, J = 7.84 Hz, 1H), 7.28
(t, J = 7.4 Hz, 1H), 7.10 (t, J = 7.4 Hz, 1H), 6.94
(d, J = 8.68 Hz, 2H), 3.73 (s, 3H); Mass (ESI): 255.1
[M+H]+.
2.2b Benzothiazol-2-yl-phenyl-amine (table 1, Entry 2):
Colourless solid; M.p.: 166–167◦C; IR (KBr, cm−1):
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3444, 3054, 1666, 1573, 1467, 1249; H NMR (400
MHz, DMSO-d6): δ 10.46 (br s, 1H, NH), 7.81–7.78
(m, 3H), 7.61–7.59 (m, 1H), 7.38–7.30 (m, 3H), 7.17–
7.714 (m, 1H), 7.04–7.00 (m, 1H);13C NMR (50 MHz,
DMSO-d6): δ 161.92, 152.46, 140.98, 130.33, 129.34,
126.21, 122.62, 122.40, 121.39, 119.56, 118.11; Mass
(ESI): 227.2 [M+H]+.
2.2i Benzooxazol-2-yl-(2,3-dimethyl-phenyl)-amine (table 1,
Entry 9): solid; M.p.: 140–141◦C; IR (KBr, cm−1):
3445, 3146, 2852, 1664, 1580, 1473, 1264; H NMR
(400 MHz, DMSO-d6): δ 10.22 (s, 1H), 7.78–7.75 (m,
1H), 7.40–7.38 (m, 1H), 7.25–7.17 (m, 4H), 7.09–7.05
(m, 1H), 2.36 (s, 3H), 2.28 (s, 3H); 13C NMR (50 MHz,
DMSO-d6): δ 160.53, 148.03, 143.17, 137.53, 137.03,
130.39, 126.74, 125.93, 124.13, 122.16, 121.20,
116.34, 109.05, 20.57, 14.19;
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2.2c Benzooxazol-2-yl-(3-chloro-phenyl)-amine (table 1,
Entry 3): Yellow solid; M.p.: 212–213◦C; IR (KBr,
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cm−1): 3444, 3032, 1663, 1576, 1492, 1231, 1092; H
NMR (400 MHz, DMSO-d6): δ 10.50 (br s, 1H, NH),
8.15-8.13 (m, 1H), 7.65–7.61 (m, 1H), 7.45–7.05 (m,
6H); Mass (ESI): 244.9 [M+H]+.
2.2j Benzothiazol-2-yl-(2,3-dimethyl-phenyl)-amine (table
1, Entry 10): solid; M.p.: 196–197◦C; IR (KBr, cm−1):
3440, 3134, 2849, 1613, 1569, 1450; H NMR (400
MHz, DMSO-d6): δ 9.67 (br s, 1H, NH), 7.70 (d, J =
7.68 Hz, 1H), 7.44 (dd, J = 7.68, 7.89 Hz, 2H), 7.24
(t, J = 7.52 Hz, 1H), 7.14–7.03 (m, 3H), 2.27 (s, 3H),
2.15 (s, 3H); Mass (ESI): 255.0 [M+H]+.
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2.2d Benzothiazol-2-yl-(3-chloro-phenyl)-amine (table 1,
Entry 4): solid; M.p.: 237–238◦C; IR (KBr, cm−1):
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3444, 3117, 1620, 1493, 1275, 1098, 730; H NMR
(400 MHz, DMSO-d6): δ 10.61 (br s, 1H, NH), 7.81 (d,
J = 8.64 Hz, 3H), 7.60 (d, J = 7.92 Hz, 1H), 7.40 (d,
J = 8.76 Hz, 2H), 7.32 (t, J = 7.28 Hz, 1H), 7.16 (t,
J = 7.44 Hz, 1H); Mass (ESI): 261.0 [M+H]+.
2.2k Benzooxazol-2-yl-(4-nitro-phenyl)-amine (table 1,
Entry 11): solid; M.p.: 189–190◦C; H NMR (400
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MHz, DMSO-d6): δ 10.93 (br s, 1H, NH), 8.77 (s, 1H),
8.15 (d, J = 8.90 Hz, 1H), 7.75 (d, J = 8.95 Hz, 1H),
7.49–7.40 (m, 2H), 7.28 (d, J = 3.10 Hz, 1H), 7.15 (t,
J = 4.70 Hz, 1H), 7.04 (t, J = 5.51 Hz, 1H); Mass
(ESI): 256.0 [M+H]+.
2.2e Benzooxazol-2-yl-(4-fluoro-phenyl)-amine (table 1,
Entry 5): solid; M.p.: 112–113◦C; 1H NMR (400 MHz,
DMSO-d6): δ 10.62 (br s, 1H, NH), 7.77–7.73 (m, 2H),
7.47–7.41 (m, 2H), 7.22–7.09 (m, 4H); 13C NMR (100
MHz, DMSO-d6): δ 158.63, 158.00, 156.26, 147.00,
135.15, 123.98, 121.64, 119.18, 119.10, 116.54,
115.64, 115.41, 108.92; Mass (ESI): 228.8 [M+H]+.
2.2l Benzooxazol-2-yl-(3,4-dichloro-phenyl)-amine (table
1, Entry 12): solid; M.p.: 217–218◦C; IR (KBr, cm−1):
3384, 3036, 1688, 1594, 1460, 1362, 1250, 747; H
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2.2f Benzothiazol-2-yl-(4-fluoro-phenyl)-amine (table 1, NMR (400 MHz, DMSO-d6): δ 10.30 (br s, 1H), 8.05-
Entry 6): solid; M.p.: 212–213◦C; IR (KBr, cm−1): 8.03 (m, 1H), 7.69–7.63 (m, 1H), 7.44–7.42 (m, 2H),