NOVEL TRIAZOLE DERIVATIVES
2245
1261.49, 1170.83, 1026.16 (C-N stretching), 812.06, 746.48 (C-H out of plane
deformation), 669.32 (C-S stretching).
1H NMR (400 MHz) (DMSO-d6) d (ppm): 0.83–0.95 (2H, m, cyclohexane H),
1.05–1.35 (4H, m, cyclohexane H), 1.50–1.77 (7H, m, cyclohexane H, cyclohexane-C-
H2), 2.41 (3H, s, CH3), 2.67 (2H, t, J ¼ 7.8 Hz, CH2-triazole), 4.19 (2H, s, S-CH2),
5.85 (2H, s, NH2), 7.22 (1H, d, J ¼ 8.2 Hz, benzothiazole H5), 7.62 (1H, d, J ¼ 8.2 Hz,
benzothiazole H7), 7.69 (1H, s, benzothiazole H4), 12.54 (1H, m, N-H).
13C NMR (100 MHz) (DMSO-d6) d (ppm): 20.97 (CH3), 21.08 (CH2, CH2-
triazole), 25.70 (2CH2, cyclohexane), 26.10 (CH2, cyclohexane), 32.45 (2CH2,
cyclohexane), 33.43 (CH2, cyclohexane-CH2), 34.78 (CH2, S-CH2), 36.57 (CH, cyclo-
hexane C1), 120.17 (CH, benzothiazole C7), 121.05 (CH, benzothiazole C4), 127.28
(CH, benzothiazole C5), 131.62 (C, benzothiazole C7a), 132.95 (C, benzothiazole
C6), 146.46 (C, benzothiazole C3a), 150.39 (C, triazole C5), 156.67 (C, triazole C3),
=
156.74 (C, benzothiazole C2), 167.29 (C, C O).
MS (EI) m=z (%): 226 (31), 164 (100), 155 (83), 130 (73), 98 (23), 84 (45), 66
(53), 55 (24).
Anal. calc. for C20H26N6OS2: C, 55.79; H, 6.09; N, 19.52. Found: C, 55.82; H,
6.12; N, 19.54.
4-Amino-5-(2-cyclohexylethyl)-3-[N-(6-methoxybenzothiazole-2-
yl)acetamido]thio-4H-1,2,4-triazole (IIId)
Compound IIId was synthesized according to the method described for IIIa
4-amino-5-
using
N-(6-methoxybenzothiazol-2-yl)-2-chloroacetamide
and
(2-cyclohexylethyl)-2,4-dihydro-3H-1,2,4-triazol-3-thione (IIa).
IR (KBr) nmax (cmꢁ1): 3425.69, 3317.67 (amine N-H stretching), 3194.23
(amide N-H stretching), 3070.78 (aromatic C-H stretching), 2920.32 (aliphatic C-H
asymmetric stretching), 2847.03 (aliphatic C-H symmetric stretching), 1681.98
=
=
=
(amide C O stretching), 1610.61, 1564.32, 1465.95 (C N and C C stretching),
1332.86, 1259.56, 1170.83, 1062.81 (C-N stretching), 810.13, 746.48 (C-H out of
plane deformation), 671.25 (C-S stretching).
1H NMR (400 MHz) (DMSO-d6) d (ppm): 0.83–0.95 (2H, m, cyclohexane H),
1.05–1.35 (4H, m, cyclohexane H), 1.50–1.80 (7H, m, cyclohexane H, cyclohexane-C-
H2), 2.67 (2H, t, J ¼ 7.8 Hz, CH2-triazole), 3.81 (3H, s, O-CH3), 4.21 (2H, s, S-CH2),
5.90 (2H, s, NH2), 7.04 (1H, d, J ¼ 8.6 Hz, benzothiazole H5), 7.57 (1H, s, benzothia-
zole H7), 7.66 (1H, d, J ¼ 8.6 Hz, benzothiazole H4), 12.43 (1H, m, N-H).
13C NMR (100 MHz) (DMSO-d6) d (ppm): 21.00 (CH2, CH2-triazole), 25.67
(2CH2, cyclohexane), 26.09 (CH2, cyclohexane), 32.42 (2CH2, cyclohexane), 33.39
(CH2, cyclohexane-CH2), 34.56 (CH2, S-CH2), 36.52 (CH, cyclohexane C1), 55.59
(CH3), 104.70 (CH, benzothiazole C7), 114.93 (CH, benzothiazole C5), 121.21
(CH, benzothiazole C4), 132.76 (C, benzothiazole C7a), 142.58 (C, benzothiazole
C3a), 150.47 (C, triazole C5), 155.63 (C, benzothiazole C6), 156.17 (C, triazole C3),
=
156.62 (C, benzothiazole C2), 167.26 (C, C O).
MS (EI) m=z (%): 226 (44), 180 (65), 165 (78), 155 (61), 143 (21), 130 (100), 55
(20).
Anal. calc. for C20H26N6O2S2: C, 53.79; H, 5.87; N, 18.82. Found: C, 53.81; H,
5.90; N, 18.80.