DOI: 10.3109/14756366.2014.945168
2-(4-Aminophenyl)benzothiazole derivatives
3
Anal Calcd for C22H15N3OS3.3H2O: C: 54.19%, H: 4.34%, N: 4.32 (s, 2H, CH2), 7.13 (dd, J: 8.49 Hz, 1H, Ar-H), 7.43–7.47 (m,
8.62%; found C: 54.07%, H: 4.39%, N: 8.56%.
1H, Ar-H), 7.49 (dt, J: 7.62 Hz, J: 7.60 Hz, 1H, Ar-H), 7.52 (dt, J:
8.15 Hz, J: 8.14 Hz, 1H, Ar-H), 7.58 (dt, J: 8.30 Hz, J: 8.28 Hz,
1H, Ar-H), 7.68 (dd, J: 2.15 Hz, J: 2.11 Hz, 1H, Ar-H), 8.04 (d, J:
2.10 Hz, 1H, Ar-H), 8.10 (d, J: 7.96 Hz, 1H, Ar-H), 8.19 (d, J:
7.47 Hz, 1H, Ar-H), 8.28 (d, J: 8.72 Hz, 1H, Ar-H), 10.99 (s, 1H,
NH), 12.68 (s, 1H, benzimidazole NH). MS (ES+): 485 (100%)
M + 1, 486 (23%) M + 2, 487 (71.7%) M + 3. Anal Calcd for
C22H14Cl2N4OS2.1/2H2O: C: 53.44%, H: 3.04%, N: 11.34%;
found C: 53.57%, H: 3.22%, N: 11.52%.
N-[4-(Benzothiazole-2-yl)phenyl]-2-[(5-chlorobenzothia-
zole-2-yl)thio]acetamide (7)
IR (KBr) ꢀmax (cmꢁ1): 3242 (N–H), 3174 (aromatic C–H), 2951
(aliphatic C–H), 1683 (C¼O), 1545–1423 (C¼C, C¼N), 1332–
1115 (C–N). 1H-NMR (400 MHz) (DMSO-d6) ꢁ (ppm): 4.46
(s, 2H, CH2), 7.44 (m, 2H, Ar-H), 7.54 (dt, J: 8.23 Hz, J: 8.21 Hz,
1H, Ar-H), 7.81 (d, J: 8.72 Hz, 2H, Ar-H), 7.90 (d, J: 2.05 Hz, 1H,
Ar-H), 8.03 (d, J: 8.04 Hz, 1H, Ar-H), 8.07 (t, J: 7.22 Hz, 3H,
Ar-H), 8.13 (d, J: 7.94 Hz, 1H, Ar-H), 10.80 (s, 1H, NH). MS
(ES+): 468.5 (100%) M + 1, 469.5 (27%) M + 2, 470.5 (49%)
N-[4-(Benzothiazole-2-yl)-3-chlorophenyl]-2-[(5-methyl-
benzimidazole-2-yl)thio]acetamide (12)
M + 3. Anal Calcd for C22H14ClN3OS3.H2O: C: 54.37%, IR (KBr) ꢀmax (cmꢁ1): 3238 (NH), 3071 (aromatic C–H), 2917
H: 3.32%, N: 8.65%; found C: 54.30%, H: 3.19%, N: 8.81%.
(aliphatic C–H), 1672 (C¼O), 1600–1457 (C¼C, C¼N), 1342–
1034 (C–N). 1H-NMR (400 MHz)(DMSO-d6) ꢁ (ppm): 2.38
(s, 3H, CH3), 4.31 (s, 2H, CH2), 6.96 (t, J: 7.82 Hz, 1H, Ar-H),
7.25 (m, 1H, Ar-H), 7.40 (m, 1H, Ar-H), 7.50 (dt, J: 8.15 Hz,
J: 8.14 Hz, 1H, Ar-H), 7.58 (dt, J: 8.30 Hz, J: 8.28 Hz, 1H, Ar-H),
7.68 (dd, J: 2.15 Hz, J: 2.11 Hz, 1H, Ar-H), 8.04 (d, J: 2.10 Hz,
1H, Ar-H), 8.10 (d, J: 7.96 Hz, 1H, Ar-H), 8,19 (d, J: 7.47 Hz, 1H,
Ar-H), 8.28 (d, J: 8.72 Hz, 1H, Ar-H), 10.99 0 (s, 1H, NH), 12.68
(s, 1H, benzimidazole NH). MS (ES+): 465.5 (100%) M + 1,
466.5 (25.2%) M + 2, 467.5 (32%) M + 3. Anal Calcd for
C23H17ClN4OS2.H2O: C: 57.19%, H: 3.96%, N: 11.60%; found
C: 57.28%, H: 3.75%, N: 12.02%.
N-[4-(Benzothiazole-2-yl)phenyl]-2-[(benzoxazole-2-
yl)thio]acetamide (8)
IR (KBr) ꢀmax (cmꢁ1): 3325 (N–H), 3051 (aromatic C–H), 2912
(aliphatic C–H), 1674 (C¼O), 1593–1467 (C¼C, C¼N), 1312–
1024 (C–N, O–C). 1H-NMR (400 MHz) (DMSO-d6) ꢁ (ppm):
4.50 (s, 2H, CH2), 7.32–7.36 (m, 2H, Ar-H), 7.45 (dt, J: 7.58 Hz,
J: 7.56 Hz, 1H, Ar-H), 7.54 (dt, J: 6.84 Hz, J: 6.83 Hz, 1H, Ar-H),
7.63–7.69 (m, 2H, Ar-H), 7.82 (d, J: 8.74 Hz, 2H, Ar-H), 8.03
(d, J: 2.68 Hz, 1H, Ar-H), 8.09 (d, J: 8.77 Hz, 2H, Ar-H), 8.14
(d, J: 7.82 Hz, 1H, Ar-H), 10.82 (1H, s, NH). MS (ES+): 418
(100%) M + 1, 419 (20%) M + 2, 420 (14%) M + 3. Anal Calcd for
C22H15N3O2S2.4H2O: C: 53.97%, H: 4.70%, N: 8.58%; found C:
54.06%, H: 4.68%, N: 8.51%.
N-[4-(Benzothiazole-2-yl)-3-chlorophenyl]-2-[(benzothia-
zole-2-yl)thio]acetamide (13)
IR (KBr) ꢀmax (cmꢁ1): 3249 (NH), 3049 (aromatic C–H), 2945
(aliphatic C–H), 1690 (C¼O), 1602–1457 (C¼C, C¼N), 1343–
N-[4-(Benzothiazole-2-yl)phenyl]-2-[(5-methylbenzoxa-
zole-2-yl)thio]acetamide (9)
1
1021 (C–N). H-NMR (400 MHz) (DMSO-d6) ꢁ (ppm):4.47 (s,
2H, CH2), 7.38 (t, J: 7.85 Hz, 1H, Ar-H), 7.50 (m, 2H, Ar-H) 7.59
(t, J: 8.08 Hz, 1H, Ar-H), 7.69 (dd, J: 1.92 Hz, J: 1.99 Hz, 1H, Ar-
H), 7.85 (d J: 8.02 Hz, 1H, Ar-H), 8.04 (m, 2H, Ar-H), 8.10 (d, J:
8.07 Hz, 1H, Ar-H), 8.19 (d, J: 7.99 Hz, 1H, Ar-H), 8.29 (d, J:
8.71 Hz, 1H, Ar-H), 10.94 (s, 1H, NH). MS (ES+): 468 (100%)
M + 1, 469 (24%) M + 2, 470 (52%) M + 3, 471 (14%) M + 4.
Anal Calcd for C22H14ClN3OS3: C: 56.46%, H: 3.03%, N: 8.98%;
found C: 56.38%, H: 3.01%, N: 8.93%.
IR (KBr) ꢀmax (cmꢁ1): 3261 (N–H), 3057 (aromatic C–H), 2900
(aliphatic C–H), 1697 (C¼O), 1548–1429 (C¼C, C¼N), 1349–
1028 (C–N, C–O). 1H-NMR (400 MHz) (DMSO-d6) ꢁ (ppm):
2.40 (s, 3H, CH3), 4.15 (s, 2H, CH2), 7.14 (d, J: 7.22 Hz, 1H,
Ar-H), 7.45 (m, 2H, Ar-H), 7.55 (m, 2H, Ar-H), 7.81 (d, J:
8.73 Hz, 2H, Ar-H), 8.04 (d, J: 8.01 Hz, 1H, Ar-H), 8.08 (d, J:
6.07 Hz, 2H, Ar-H), 8.13 (d, J: 7.93 Hz, 1H, Ar-H), 10.80 (s, 1H,
NH). MS (ES+): 432 (100%) M + 1, 433 (26%) M + 2, 434
(13.2%) M + 3. Anal Calcd for C23H17N3O2S2.H2O: C: 61.45%,
H: 4.26%, N: 9.35%; found C: 61.32%, H: 4.09%, N: 9.61%.
N-[4-(Benzothiazole-2-yl)-3-chlorophenyl]-2-[(benzoxa-
zole-2-yl)thio]acetamide (14)
IR (KBr) ꢀmax (cmꢁ1): 3232 (NH), 3066 (aromatic C–H), 2961
(aliphatic C–H), 1666 (C¼O), 1589–1457 (C¼C, C¼N), 1325–
1018 (C–N, O–C). 1H-NMR (400 MHz) (DMSO-d6) ꢁ (ppm):
4.50 (s, 2H, CH2), 7.32–7.36 (m, 2H, Ar-H), 7.63–7.69 (m, 2H,
Ar-H), 7.70 (dt, J: 8.15 Hz, J: 8.14 Hz, 1H, Ar-H), 7.78 (dt, J:
8.30 Hz, J: 8.28 Hz, 1H, Ar-H), 7.88 (dd, J: 2.13 Hz, J: 2.08 Hz,
1H, Ar-H), 8.04 (d, J: 2.10 Hz, 1H, Ar-H), 8.10 (d, J: 7.96 Hz, 1H,
Ar-H), 8,19 (d, J: 7.47 Hz, 1H, Ar-H), 8.28 (1H, d, J: 8.72 Hz,
Ar-H), 10.99 (s, 1H, NH). MS (ES+): 451.5 (100%) M + 1, 452.5
(25.7%) M + 2, 453.5 (42.8%) M + 3. Anal Calcd for
C22H14ClN3O2S2: C: 58.47%, H: 3.12%, N: 9.30%; found
C: 58.54%, H: 3.01%, N: 9.14%.
N-[4-(Benzothiazole-2-yl)-3-chlorophenyl]-2-[(benzimida-
zole-2-yl)thio]acetamide (10)
IR(KBr) ꢀmax (cmꢁ1): 3434 (N–H), 3051 (aromatic C–H), 2986
(aliphatic C–H), 1677 (C¼O), 1599–1497 (C¼C, C¼N), 1326–
1045 (C–N). 1H-NMR (400 MHz) (DMSO-d6) ꢁ (ppm): 4.34
(s, 2H, CH2), 7.13 (m, 2H, Ar-H), 7.45 (m, 2H, Ar-H), 7.50 (dt, J:
8.15 Hz, J: 8.14 Hz, 1H, Ar-H), 7.58 (dt, J: 8.30 Hz, J: 8.28 Hz,
1H, Ar-H), 7.68 (dd, J: 2.15 Hz, J: 2.11 Hz, 1H, Ar-H), 8.04 (d, J:
2.10 Hz, 1H, Ar-H), 8.10 (d, J: 7.96 Hz, 1H, Ar-H), 8,19 (d, J:
7.47 Hz, 1H, Ar-H), 8.28 (d, J: 8.72 Hz, 1H, Ar-H), 10.99 (s, 1H,
NH), 12.68 (s, 1H, benzimidazole NH). MS (ES+): 451 (100%)
M + 1, 452 (24%) M + 2, 453 (40%) M + 3. Anal Calcd for
C22H15ClN4OS2.1/4H2O: C: 58.02%, H: 3.30%, N: 12.31%; found
C: 57.92%, H: 3.28%, N: 12.28%.
N-[4-(Benzothiazole-2-yl)-3-chlorophenyl]-2-[(5-methyl-
benzoxazole-2-yl)thio]acetamide (15)
IR (KBr) ꢀmax (cmꢁ1): 3247 (NH), 3064 (aromatic C–H), 2963
(aliphatic C–H), 1687 (C¼O), 1527–1345 (C¼C, C¼N), 1350–
1076 (C–N, O–C). 1H-NMR (400 MHz) (DMSO-d6) ꢁ (ppm):
N-[4-(Benzothiazole-2-yl)-3-chlorophenyl]-
2-[(5-chlorobenzimidazole-2-yl)thio]acetamide (11)
IR (KBr) ꢀmax (cmꢁ1): 3290 (N–H), 3054 (aromatic C–H), 2929 2.40 (s, 3H, CH3), 4.15 (s, 2H, CH2), 7.14 (d, J: 7.22 Hz, 1H,
(aliphatic C–H), 1677 (C¼O), 1596–1454 (C¼C, C¼N), Ar-H), 7.45 (m, 2H, Ar-H), 7.50 (dt, J: 8.15 Hz, J: 8.14 Hz, 1H,
1334–1021 (C–N). 1H-NMR (400 MHz) (DMSO-d6) ꢁ (ppm): Ar-H), 7.58 (dt, J: 8.30 Hz, J: 8.28 Hz, 1H, Ar-H), 7.68 (dd, J: