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to Kaberdin et al.42 mp 137–138 ꢀC (lit.42 134–135 ꢀC, lit.12 138–
139 ꢀC). Spectroscopic data are in accordance with those
reported previously.12,42
1,10-(4-Bromo-3,4-dichloro-2-nitrobuta-1,3-diene-1,1-diyl)bis(1H-
benzo[d][1,2,3]triazole) (2b). 2b was prepared in ether according
to Kaberdin et al.42 mp 127–128 ꢀC (lit.42 124–126 ꢀC).
Spectroscopic data are in accordance with those reported
previously.42
1,10-(4-Bromo-3,4-dichloro-2-nitrobuta-1,3-diene-1,1-diyl)bis(5-
chloro-1H-benzo[d][1,2,3]triazole) (2c). 2c was prepared in ether
according to Kaberdin et al.42 2.606 g, 50%, mp 141–142.5 ꢀC. IR
(ATR) n (cmꢂ1): 3085, 3065 (CHaromatic), 1458, 1450 (C]C), 1590,
1245 (NO2), 1077, 947. 1H NMR (500 MHz, CDCl3) d ¼ 7.29–7.38
(m, 2H, CHaromatic), 7.69–7.87 (m, 2H, CHaromatic), 8.26–8.36 (m,
2H, CHaromatic). 13C NMR (125 MHz, CDCl3) d ¼ 115.89, 115.83,
118.13, 128.62, 129.33 (CHaromatic), 114.85 (C4), 120.58 (C3),
132.67, 132.92, 141.26, 143.09, 149.41, 149.51 (Caromatic), 135.41
(C2), 179.98 (C1). MS (ESI+): m/z (%) 574 (51, [M + Na]+). Anal.
calcd for C16H6BrCl4N7O2 (549.981) (%): C, 34.94; H, 1.10; N,
17.83. Found (%): C, 35.15; H, 1.01; N, 18.06%.
N-((Z)-1-(1H-Benzo[d][1,2,3]triazol-1-yl)-4-bromo-2,4-dichloro-
3-nitrobuta-1,3-dien-1-yl)-4-(hexyloxy)aniline (3c). According to
the general experimental method with 2b (0.71 mmol) and 4-
(hexyloxy)aniline (0.75 mmol). 0.3101 g, 79%, mp 113–115 ꢀC. IR
(ATR) n (cmꢂ1): 3325 (NH), 3045 (CHaromatic), 2961, 2924, 2856
(CHaliphatic), 1659, 1489, 1449 (C]C), 1529, 1361, 1262 (NO2),
1100, 1020, 802. 1H NMR (500 MHz, CDCl3) d ¼ 0.85 (t, 3J ¼ 6.83
Hz, 3H, CH3), 1.14–1.44 (m, 6H, (CH2)3), 1.76 (p, 2H, CH2), 3.99
(t, 3J ¼ 6.83 Hz, 2H, OCH2), 7.26 (d, 3J ¼ 2.44 Hz, 1H, CHaromatic),
3
7.28 (d, J ¼ 2.93 Hz, 1H, CHaromatic), 7.45–7.50 (m, 4H, CHar-
3
omatic), 7.67 (t, J ¼ 2.93 Hz, 2H, CHaromatic), 7.92 (broad s, 1H,
NH). 13C NMR (125 MHz, CDCl3) d ¼ 13.03 (CH3), 21.57, 24.64,
27.90, 30.49 (CH2)4, 68.04 (OCH2), 100.43 (C4), 117.64 (C3),
123.81, 125.32, 126.40, 130.87 (CHaromatic), 114.00, 130.81,
134.43, 154.58 (Caromatic), 133.44 (C2), 155.91 (C1). MS (ESI+): m/z
(%) 553 (16, [M]+), 517 (100, [M ꢂ Cl]+), 435 (27, [M ꢂ Bzt]+). Anal.
calcd for C22H22BrCl2N5O3 (555.252) (%): C, 47.59; H, 3.99; N,
12.61. Found (%): C, 47.57; H, 4.28; N, 12.87.
N-((Z)-1-(1H-Benzo[d][1,2,3]triazol-1-yl)-4-bromo-2,4-dichloro-
3-nitrobuta-1,3-dien-1-yl)-4-(octyloxy)aniline (3d). According to
the general experimental method with 2b (0.73 mmol) and 4-
ꢀ
(octyloxy)aniline (0.77 mmol). 0.348 g, 82%, mp 128–130 C. IR
General experimental method46 for preparation of amino
substituted benzotriazolyl derivatives (3a–e)
(ATR) n (cmꢂ1): 3280 (NH), 3010 (CHaromatic), 2960, 2922, 2852
(CHaliphatic), 1643, 1492, 1456 (C]C), 1531, 1364, 1261 (NO2),
1105, 1030, 796. 1H NMR (500 MHz, CDCl3) d ¼ 0.82 (t, 3J ¼ 7.32
Hz, 3H, CH3), 1.17–1.44 (m, 10H, (CH2)5), 1.76 (p, 2H, CH2), 3.98
(t, 3J ¼ 6.34 Hz, 2H, OCH2), 7.27 (d, 3J ¼ 2.92 Hz, 1H, CHaromatic),
(Z)-N-(1-(1H-Benzo[d][1,2,3]triazol-1-yl)-2,4,4-trichloro-3-nitro-
buta-1,3-dien-1-yl)-4-(hexyloxy)aniline (3a). 3a was synthesized in
MeOH according to Kaufmann et al.46 0.544 g, 71%. IR (ATR) n
(cmꢂ1): 3324 (NH), 3081, 3050 (CHaromatic), 2961, 2924, 2854
(CHaliphatic), 1651, 1467, 1452 (C]C), 1510, 1365, 1261 (NO2),
1096, 1024, 800. 1H NMR (500 MHz, CDCl3) d ¼ 0.84 (t, 3J ¼ 6.83
Hz, 3H, CH3), 1.15–1.42 (m, 6H, (CH2)3), 1.74 (p, 2H, CH2), 3.97 (t,
3J ¼ 6.83 Hz, 2H, OCH2), 7.34–7.36 (m, 3H, CHaromatic), 7.40–7.46
(m, 3H, CHaromatic), 7.73–7.75 (m, 2H, CHaromatic), 7.79 (broad s,
1H, NH). 13C NMR (125 MHz, CDCl3) d ¼ 12.99 (CH3), 24.64,
27.95, 28.68, 30.51 (CH2)4, 67.94 (OCH2), 101.24 (C4), 116.71 (C3),
124.18, 125.04, 127.03, 129.46 (CHaromatic), 113.97, 130.99,
138.09, 155.58 (Caromatic), 137.73 (C2), 156.62 (C1). MS (ESI+): m/z
(%) 337 (100, [M ꢂ Bzt ꢂ C4H9]+). Anal. calcd for C22H22Cl3N5O3
(510.801) (%): C, 51.73; H, 4.34; N, 13.71. Found (%): C, 51.57; H,
4.30; N, 13.96.
3
7.29 (d, J ¼ 2.44 Hz, 1H, CHaromatic), 7.49–7.50 (m, 4H, CHar-
3
omatic), 7.67 (t, J ¼ 2.93 Hz, 2H, CHaromatic), 7.96 (broad s, 1H,
NH). 13C NMR (125 MHz, CDCl3) d ¼ 14.33 (CH3), 22.88, 26.21,
29.18, 29.44, 29.52, 32.03 (CH2)6, 69.28 (OCH2), 101.65 (C4),
118.94 (C3), 120.27, 122.26, 126.60, 132.06 (CHaromatic), 113.62,
132.12, 135.64, 155.87 (Caromatic), 134.65 (C2), 157.15 (C1). MS
(ESI+): m/z (%) 606 (20, [M + Na]+), 545 (46, [M ꢂ Cl]+), 534 (22, [M
ꢂ NO2]+), 465 (100, [M ꢂ Bzt]+). Anal. calcd for C24H26BrCl2N5O3
(583.305) (%): C, 49.42; H, 4.49; N, 12.01. Found (%): C, 49.65; H,
4.60; N, 11.78.
N-((Z)-4-Bromo-2,4-dichloro-1-(5-chloro-1H-benzo[d][1,2,3]-
triazol-1-yl)-3-nitrobuta-1,3-dien-1-yl)-4-methoxyaniline
(3e).
According to the general experimental method with 2c (0.36
mmol) and 4-methoxyaniline (0.38 mmol). 0.1392 g, 74%. IR
(ATR) n (cmꢂ1): 3483, 3409 (NH), 3045 (CHaromatic), 2786 (CHa-
liphatic), 1655, 1493 (C]C), 1361, 1281, 1200 (NO2), 797. 1H NMR
(500 MHz, CDCl3) d ¼ 3.86 (s, 3H, OCH3), 7.29 (d, 3J ¼ 2.93 Hz,
1H, CHaromatic), 7.31 (d, 3J ¼ 2.44 Hz, 1H, CHaromatic), 7.35 (d, 3J
¼ 1.95 Hz, 1H, CHaromatic), 7.36 (d, 3J ¼ 1.47 Hz, 1H, CHaromatic),
(Z)-N-(1-(1H-Benzo[d][1,2,3]triazol-1-yl)-2,4,4-trichloro-3-nitro-
buta-1,3-dien-1-yl)-4-(octyloxy)aniline (3b). According to the
general experimental method with 2a (1.16 mmol) and 4-(octy-
loxy)aniline (1.22 mmol). 0.4206 g, 67%. IR (ATR) n (cmꢂ1): 3225
(NH), 3054 (CHaromatic), 2961, 2924, 2853 (CHaliphatic), 1672, 1531,
1
1465 (C]C), 1509, 1358, 1261, 1210 (NO2), 1096, 1023, 704. H
NMR (500 MHz, CDCl3) d ¼ 0.82 (t, 3J ¼ 6.83 Hz, 3H, CH3), 1.19–
3
3
7.52 (d, J ¼ 9.27 Hz, 2H, CHaromatic), 7.71 (t, J ¼ 2.93 Hz, 2H,
3
CHaromatic), 7.81 (s, 1H, CHaromatic), 7.83 (broad s, 1H, NH). 13
C
1.40 (m, 10H, (CH2)5), 1.65 (p, 2H, CH2), 3.96 (t, J ¼ 6.83 Hz,
2H, OCH2), 7.09–7.24 (m, 3H, CHaromatic), 7.36–7.45 (m, 3H,
CHaromatic), 7.73–7.75 (m, 2H, CHaromatic), 7.80 (broad s, 1H, NH).
13C NMR (125 MHz, CDCl3) d ¼ 13.06 (CH3), 21.62, 24.97, 28.19,
28.29, 28.69, 30.78 (CH2)6, 67.93 (OCH2), 101.19 (C4), 116.70 (C3),
121.93, 125.47, 127.08, 129.47 (CHaromatic), 113.86, 126.96,
131.00, 155.55 (Caromatic), 129.01 (C2), 156.63 (C1). MS (ESI+): m/z
(%) 383 (59, [M ꢂ Bzt ꢂ Cl]+). Anal. calcd for C24H26Cl3N5O3
(538.854) (%): C, 53.49; H, 4.86; N, 13.00. Found (%): C, 53.15; H,
4.70; N, 12.87.
NMR (125 MHz, CDCl3) d ¼ 55.11 (OCH3), 99.94 (C4), 115.69
(C3), 117.65, 123.58, 125.42, 126.17 (CHaromatic), 112.55, 125.41,
130.84, 134.57, 154.55 (Caromatic), 131.69 (C2), 156.42 (C1). MS
(ESI+): m/z (%) 515 (100, [M ꢂ H]+), 483 (30, [M ꢂ Cl]+). MS (ESI +
MS/MS): m/z (%) 515 (45, [M ꢂ H]+), 367 (61, [M ꢂ (5-chloro-
Bzt)]+), 335 (100, [M ꢂ (5-chloro-Bzt) ꢂ OCH3]+). Anal. calcd for
C
17H11BrCl3N5O3 (519.564) (%): C, 39.30; H, 2.13; N, 13.48.
Found (%): C, 38.95; H, 2.40; N, 13.71.
This journal is © The Royal Society of Chemistry 2014
RSC Adv., 2014, 4, 19640–19645 | 19643