DOI: 10.3109/14756366.2013.763253
N-[4-(2-methylthiazol-4-yl)phenyl]acetamide derivatives 177
2-[(1H-Benzimidazole-2-yl)sulfanyl]-N-[4-(2-methylthiazol-
4-yl)phenyl]acetamide (6e)
10.56 (s, 1H, N–H). For C19H15N3O2S2 calculated: 59.82% C,
3.96% H and 11.02% N; found: 59.82% C, 3.98% H and 11.05%
N. MS [M þ 1]þ: m/z 382.
Yield 76%; m.p. 241 ꢀC. IR (KBr) ꢀmax (cmꢁ1): 3274 (amide
N–H), 3012 (aromatic C–H), 2973 (aliphatic C–H), 1681 (amide
C¼O), 1549–1399 (C¼C and C¼N) and 1268–984 (C–N).
1H-NMR (500 MHz, DMSO-d6) ꢁ (ppm): 2.70 (s, 3H, CH3), 4.30
2-[(5-Chlorobenzoxazole-2-yl)sulfanyl]-N-[4-(2-methylthia-
zol-4-yl)phenyl]acetamide (6j)
(s, 2H, S–CH2), 7.46 (brs, 2H, Ar-H), 7.12–7.15 (m, 2H, Ar-H), Yield 82%; m.p. 129 ꢀC. IR (KBr) ꢀmax (cmꢁ1): 3276 (amide
7.65 (d, 2H, J ¼ 8.15 Hz, Ar-H), 7.81 (s, 1H, thiazole C5-H), 7.89 N–H), 3053 (aromatic C–H), 2949 (aliphatic C–H), 1676 (amide
(d, 2H, J ¼ 8.32 Hz, Ar-H), 10.62 (s, 1H, N–H) and 12.67 (s, 1H, C¼O), 1598–1422 (C¼C and C¼N) and 1310–1005 (C–N and
benzimidazole N–H). For C19H16N4OS2 calculated: 59.98% C, C–O). 1H-NMR (500 MHz, DMSO-d6): 2.71 (s, 3H, CH3), 4.39 (s,
4.24% H and 14.73% N; found: 59.96% C, 4.23% H and 14.75% 2H, S–CH2), 7.38 (d, 1H, J ¼ 8.55 Hz, Ar-H), 7.65 (d, 2H,
N. MS [M þ 1]þ: m/z 381.
J ¼ 8.80 Hz, Ar-H), 7.72–7.75 (m, 2H, Ar-H), 7.81 (s, 1H,
thiazole C5–H), 7.89 (d, 2H, J ¼ 8.40 Hz, Ar-H) and 10.59 (s, 1H,
N–H). For C19H14ClN3O2S2 calculated: 54.87% C, 3.39% H and
10.10% N; found: 54.89% C, 3.40% H and 10.13% N. MS
[M þ 1]þ: m/z 416.5.
2-[(5-Chloro-1H-benzimidazole-2-yl)sulfanyl]-N-[4-(2-
methylthiazol-4-yl)phenyl]acetamide (6f)
Yield 86%; m.p. 233 ꢀC. IR (KBr) ꢀmax (cmꢁ1): 3269 (amide
N–H), 3053 (aromatic C–H), 2953 (aliphatic C–H), 1682 (amide
C¼O), 1576–1395 (C¼C and C¼N) and 1305–996 (C–N).
1H-NMR (500 MHz, DMSO-d6) ꢁ (ppm): 2.71 (s, 3H, CH3), 4.31
2-[(5-Methylbenzoxazole-2-yl)sulfanyl]-N-[4-(2-
methylthiazol-4-yl)phenyl]acetamide (6k)
(s, 2H S-CH2), 7.16 (dd, 1H, J ¼ 8.35 Hz and 7.92 Hz, Ar-H), 7.46 Yield 79%; m.p. 158 ꢀC. IR (KBr) ꢀmax (cmꢁ1): 3281 (amide
(d, 1H, J ¼ 7.96 Hz, Ar-H), 7.52 (s, 1H, Ar-H), 7.65 (d, 2H, N–H), 3024 (aromatic C–H), 2976 (aliphatic C–H), 1678 (amide
J ¼ 8.20 Hz, Ar-H), 7.81 (s, 1H, thiazole C5–H), 7.89 (d, 2H, C¼O), 1598–1409 (C¼C and C¼N) and 1299–1006 (C–N and
J ¼ 8.35 Hz, Ar-H), 10.56 (s, 1H, N–H) and 12.86 (s, 1H, C–O). 1H-NMR (500 MHz, DMSO-d6) ꢁ (ppm): 2.40 (s, 3H,
benzimidazole N–H). For C19H15ClN4OS2 calculated: 55.00% C, CH3), 2.70 (s, 3H, CH3), 4.39 (s, 2H, S–CH2), 7.13 (d, 1H,
3.64% H and 13.50% N; found: 55.04% C, 3.63% H and 13.51% J ¼ 8.45 Hz, Ar-H), 7.43 (s, 1H, Ar-H), 7.52 (d, 1H, J ¼ 8.50 Hz,
N. MS [M þ 1]þ: m/z 415.5.
Ar-H), 7.65 (d, 2H, J ¼ 8.30 Hz, Ar-H), 7.81 (s, 1H, thiazole C5–
H), 7.89 (d, 2H, J ¼ 8.35 Hz, Ar-H) and 10.54 (1H, s, N–H). For
C20H17N3O2S2 calculated: 60.74% C, 4.33% H and 10.62% N;
found: 60.73% C, 4.36% H and 10.61% N. MS [M þ 1]þ: m/z 396.
2-[(5-Methyl-1H-benzimidazole-2-yl)sulfanyl]-N-[4-(2-
methylthiazol-4-yl)phenyl]acetamide (6g)
Yield 90%; m.p. 106 ꢀC. IR (KBr) ꢀmax (cmꢁ1): 3268 (amide
N–H), 3042 (aromatic C–H), 2969 (aliphatic C–H), 1686 (amide
C¼O), 1546–1419 (C¼C and C¼N) and 1279–1022 (C–N).
2-[(5-Nitrobenzoxazole-2-yl)sulfanyl]-N-[4-(2-methylthia-
zol-4-yl)phenyl]acetamide (6l)
1H-NMR (500 MHz, DMSO-d6) ꢁ (ppm): 2.39 (s, 3H, CH3), 2.70 Yield 84%; m.p. 218 ꢀC. IR (KBr) ꢀmax (cmꢁ1): 3268 (amide
(s, 3H, CH3), 4.27 (s, 2H, S–CH2), 6.96 (d, 1H, J ¼ 8.50 Hz, Ar- N–H), 3046 (aromatic C–H), 2994 (aliphatic C–H), 1669 (amide
H), 7.25 (s, 1H, Ar-H), 7.35 (d, 1H, J ¼ 8.15 Hz, Ar-H), 7.65 (d, C¼O), 1596–1400 (C¼C and C¼N) and 1302–1015 (C–N and
2H, J ¼ 8.55 Hz, Ar-H), 7.81 (s, 1H, thiazole C5–H), 7.87 (d, 2H, C–O). 1H-NMR (500 MHz, DMSO-d6) ꢁ (ppm): 2.70 (s, 3H,
J ¼ 8.20 Hz, Ar-H), 10.59 (s, 1H, N–H) and 12.54 (s, 1H, CH3), 4.48 (s, 2H, S–CH2), 7.65 (d, 2H, J ¼ 8.35 Hz, Ar-H), 7.82
benzimidazole N–H). For C20H18N4OS2 calculated: 60.89% C, (s, 1H, thiazole C5–H), 7.89–7.93 (m, 3H, Ar-H), 8.26 (dd, 1H,
4.60% H and 14.20% N; found: 60.87% C, 4.63% H and 14.22% J ¼ 8.25 Hz and J ¼ 4.15 Hz, Ar-H), 8.48 (d, 1H, J ¼ 4.60 Hz, Ar-
N. MS [M þ 1]þ: m/z 395.
H) and 10.54 (s, 1H, N–H). For C19H14N4O4S2 calculated:
53.51% C, 3.31% H and 13.14% N; found: 53.54% C, 3.35% H
and 13.17% N. MS [M þ 1]þ: m/z 427.
2-[(5-Nitro-1H-benzimidazole-2-yl)sulfanyl]-N-[4-(2-
methylthiazol-4-yl)phenyl]acetamide (6h)
2-[(Benzothiazole-2-yl)sulfanyl]-N-[4-(2-methylthiazol-4-
yl)phenyl]acetamide (6m)
Yield 78%; m.p. 207 ꢀC (dekomp.). IR (KBr) ꢀmax (cmꢁ1): 3296
(amide N–H), 3042 (aromatic C–H), 2976 (aliphatic C–H), 1689
(amide C¼O), 1604–1412 (C¼C and C¼N) and 1330–1064 Yield 87%; m.p. 130 ꢀC. IR (KBr) ꢀmax (cmꢁ1): 3277 (amide
(C–N). 1H-NMR (500 MHz, DMSO-d6) ꢁ (ppm): 2.70 (s, 3H, N–H), 3039 (aromatic C–H), 2975 (aliphatic C–H), 1676 (amide
CH3), 4.38 (s, 2H, S–CH2), 7.62 (d, 1H, J ¼ 7.96 Hz, Ar-H), 7.66 C¼O), 1569–1408 (C¼C and C¼N) and 1295–1011 (C–N).
(d, 2H, J ¼ 8.20 Hz, Ar-H), 7.81 (s, 1H, thiazole C5–H), 7.89 (d, 1H-NMR (500 MHz, DMSO-d6) ꢁ (ppm): 2.70 (s, 3H, CH3), 4.42
2H, J ¼ 8.35 Hz, Ar-H), 8.07 (dd, 1H, J ¼ 8.10 Hz and 7.97 Hz, (s, 2H, S–CH2), 7.37 (t, 1H, J ¼ 7.56 Hz, Ar-H), 7.47 (t, 1H,
Ar-H), 8.32 (s, 1H, Ar-H), 10.63 (s, 1H, N–H) and 12.63 (s, 1H, J ¼ 7.52 Hz, Ar-H), 7.66 (d, 2H, J ¼ 7.82, Ar-H), 7.82 (s, 1H,
benzimidazole N–H). For C19H15N5O3S2 calculated: 53.63% C, thiazole C5–H), 7.84 (d, 1H, J ¼ 8.50 Hz, Ar-H), 7.90 (d, 2H,
3.55% H and 16.46% N; found: 53.61% C, 3.57% H and 16.45% J ¼ 8.35 Hz, Ar-H), 8.03 (d, 1H, J ¼ 8.32 Hz, Ar-H) and 10.54 (s,
N. MS [M þ 1]þ: m/z 426.
1H, N–H). For C19H15N3OS3 calculated: 57.40% C, 3.80% H and
10.57% N; found: 57.42% C, 3.83% H and 10.54% N. MS
[M þ 1]þ: m/z 427.
2-[(Benzoxazole-2-yl)sulfanyl]-N-[4-(2-methylthiazol-4-
yl)phenyl]acetamide (6i)
2-[(5-Chlorobenzothiazole-2-yl)sulfanyl]-N-[4-(2-
methylthiazol-4-yl)phenyl]acetamide (6n)
Yield 83%; m.p. 148 ꢀC. IR (KBr) ꢀmax (cmꢁ1): 3269 (amide
N–H), 3037 (aromatic C–H), 2989 (aliphatic C–H), 1667 (amide
C¼O), 1602–1450 (C¼C and C¼N) and 1301–1055 (C–N and Yield 75%; m.p. 195 ꢀC. IR (KBr) ꢀmax (cmꢁ1): 3294 (amide
C–O). 1H-NMR (500 MHz, DMSO-d6): 2.71 (s, 3H, CH3), 4.41 (s, N–H), 3015 (aromatic C–H), 2986 (aliphatic C–H), 1659 (amide
2H, S–CH2), 7.33–7.37 (m, 2H, Ar-H), 7.62–7.67 (m, 4H, Ar-H), C¼O), 1593–1402 (C¼C and C¼N) and 1296–1023 (C–N).
7.81 (s, 1H, thiazole C5–H), 7.90 (d, 2H, J ¼ 8.35 Hz, Ar-H) and 1H-NMR (500 MHz, DMSO-d6) ꢁ (ppm): 2.71 (s, 3H, CH3), 4.44