1H-1,2,3-Benzotriazole-5-carboxaldehyde
2593
N-(1H-1,2,3-benzotriazol-5-ylmethyl)-N-phenylamine (6a): mp ¼ 165–
1
1688C. H NMR (300 MHz, d6-DMSO) d 7.61 (s, 1H), 7.58 (s, 1H), 6.97–
7.05 (m, 3H), 6.62 (dd, J ¼ 0.9, 8.7 Hz, 2H), 6.48 (tt, J ¼ 0.9, 7.4 Hz, 1H),
6.14 (br s, 1H), 4.31 (s, 2H); 13C NMR (75 MHz, d6-DMSO) d 148.9, 144.4
(br), 143.9 (br), 131.5, 128.6, 120.2, 115.4, 115.3, 113.7, 112.2, 47.2; MS
MHþ ¼ 225; HRMS (EI) m/z calcd. for C13H13N4 (MHþ): 225.2674.
Found: 225.2670.
N-(1H-1,2,3-benzotriazol-5-ylmethyl)-N-benzylamine dihydrochloride (6b):
mp ¼ 1758C (decomp.). 1H NMR (300 MHz, d6-DMSO) d 10.01 (br s, 1H), 8.18
(s, 1H), 7.94 (d, J ¼ 8.5 Hz, 1H), 7.65 (dd, J ¼ 1.3, 8.5Hz, 1H), 7.56–7.60
(m, 2H), 7.37–7.45 (m, 3H), 4.32 (t, J ¼ 5.7 Hz, 2H), 4.15 (t, 5.7 Hz, 2H);
13C NMR (75 MHz, d6-DMSO) d 140.0 (br), 138.6 (br), 131.9, 130.0, 129.1,
128.7, 128.5, 127.4, 117.0, 114.9, 49.6 (two signals); MS MHþ ¼ 239; HRMS
(EI) m/z calcd. for C14H15N4 (MHþ): 239.2945. Found: 239.2944.
N-(1H-1,2,3-benzotriazol-5-ylmethyl)-N-(3-methoxypropyl)amine dihydro-
chloride (6c): mp ¼ 137–1388C. 1H NMR (300MHz, d6-DMSO) d 9.67 (br s,
bound HCl and two N-H, 4H), 8.19 (s, 1H), 7.94 (d, J ¼ 8.5 Hz, 1H), 7.67 (dd,
J ¼ 1.5, 8.5 Hz, 1H), 4.29 (t, J ¼ 5.6 Hz, 2H), 3.37 (t, J ¼ 6.0 Hz, 2H), 3.20
(s, 3H), 2.90 (m, 2H), 1.94 (m, 2H); 13C NMR (75 MHz, d6-DMSO) d 138.6
(two signals), 129.3, 127.3, 116.9, 115.0, 68.8, 57.8, 49.7, 44.0, 25.5; MS
MHþ ¼ 221; HRMS (EI) m/z calcd. for C11H17N4O (MHþ): 221.2764.
Found: 221.2767.
4-f2-[(1H-1,2,3-benzotriazol-5-ylmethyl)amino]ethylgbenzenesulfonamide
(6d): mp ¼ 173–1758C. 1H NMR (300 MHz, d6-DMSO) d 8.34 (s, 1H), 7.90
(s, 1H), 7.64 (d, J ¼ 8.5 Hz, 1H), 7.60 (AXA0X0, J ¼ 8.3 Hz, 4H), 7.52 (dd,
J ¼ 1.3, 8.5 Hz, 1H), 3.81 (t, J ¼ 7.0 Hz, 2H), 3.01 (t, J ¼ 7.0 Hz, 2H); 13C
NMR (75 MHz, d6-DMSO) d 145.4, 144.4, 144.1, 141.8, 129.2, 128.8,
125.5, 119.0, 118.2, 115.6, 61.4, 52.8, 49.8; MS MHþ ¼ 332; HRMS (EI)
m/z calcd. for C15H18N5O2S (MHþ): 332.3990. Found: 332.3993.
N-(1H-1,2,3-benzotriazol-5-ylmethyl)-N-(3,4-dimethoxyphenyl)amine
(6e): 1H NMR (300 MHz, d6-DMSO) d 15.6 (br s, 1H), 7.86 (d, J ¼ 8.7 Hz,
1H), 7.81 (s, 1H), 7.44 (d, J ¼ 8.7 Hz, 1H), 6.65 (d, J ¼ 8.7 Hz, 1H), 6.36
(d, J ¼ 2.5 Hz, 1H), 6.04 (dd, J ¼ 2.5, 8.7 Hz, 1H), 7.44 (d, J ¼ 8.7 Hz,
1H), 4.39 (d, J ¼ 5.6 Hz, 2H), 3.65 (s, 3H), 3.58 (s, 3H); 13C NMR
(75 MHz, d6-DMSO) d 150.8, 145.0, 144.5, 141.2, 139.6 (br), 126.1 (br),
125.7, 116.0, 115.4, 112.9, 103.9, 99.8; MS MHþ ¼ 285; HRMS (EI) m/z
calcd. for C15H17N4O2 (MHþ): 285.3204. Found: 285.3207.
N-(1H-1,2,3-benzotriazol-5-ylmethyl)-5-chloropyridin-2-amine trihydro-
1
chloride (6f): mp ¼ 110–1128C. H NMR (300 MHz, d6-DMSO) d 9.00–
11.00 (br, bound HCl, 3H), 8.05 (d, J ¼ 2.3 Hz, 1H), 7.95 (s, 1H), 7.90