Med Chem Res
N-(4-(3-Fluorophenyl)thiazol-2-yl)-2-p-tolylacetamide
(9h)
4.41; Cl, 10.34; N, 8.17; O, 4.67; S, 9.35. Found: C, 63.04;
H, 4.40; S, 9.32.
Isolated yield 80 %, (off white solid), m.p. 160–162 °C, 1H
NMR (400 MHz, DMSO-d6) d (ppm): 2.27 (s, 3H), 3.73 (s,
2H), 7.12–7.23 (m, 5H), 7.46–7.49 (m, 1H), 7.68 (d,
J = 10.40 Hz, 1H), 7.73 (s, 1H), 7.75 (s, 1H), 12.50 (s,
1H). 13C NMR (100 MHz, DMSO-d6) d (ppm): 21.11(C-
23), 41.76(C-15), 109.96(C-5), 114.81(C-12), 115.01(C-
10), 122.13(C-14), 129.44(C-17, C-18, C-20, C-21),
131.20(C-13), 132.28(C-16), 136.38(C-9), 137.10(C-19),
147.95(C-4), 161.84(C-11), 164.25(C-2), 170.20(C-7).
IR(KBr, cm-1): 3,228 (N–H) 1,649 (C=O), 1,257 (C–N).
MS calcd. For C18H15FN2OS:326.3. Found: 327.0 (M?).
Anal. Calc. for C18H15FN2OS: C, 66.24; H, 4.63; F, 5.82;
N, 8.58; O, 4.90; S, 9.82. Found: C, 66.21; H, 4.60; S, 9.80.
N-(4-(3-Chlorophenyl)thiazol-2-yl)-2-m-tolylacetamide
(9k)
1
Isolated yield 74 %, (white solid), m.p. 186–188 °C, H
NMR (400 MHz, DMSO-d6) d (ppm): 2.30 (s, 3H), 3.75 (s,
2H), 7.08 (d, J = 7.48 Hz, 1H), 7.14 (d, J = 7.72 Hz, 1H),
7.16 (s, 1H), 7.22 (t, J = 7.44 Hz, 1H), 7.37–7.40 (m, 1H),
7.47 (t, J = 7.84 Hz, 1H), 7.78 (s, 1H), 7.86–7.88 (m, 1H),
7.96 (t, J = 1.80 Hz, 1H).). 13C NMR (100 MHz, DMSO-
d6) d (ppm):21.43(C-23), 42.12(C-15), 110.06(C-5), 124.64
(C-14), 125.84(C-21), 126.78(C-10), 127.94(C-19),
127.97(C-12), 128.79(C-20), 130.31(C-13), 131.14(C-17),
134.05(C-9), 135.21(C-11), 136.75(C-16), 137.97(C-18),
147.67(C-4), 158.55(C-2), 170.06(C-7). IR(KBr, cm-1):
3,404 (N–H), 1,647 (C=O), 1,321 (C–N). MS calcd. For
C18H15ClN2OS 342.84. Found: 343.0. Anal. Calc. for
C18H15ClN2OS C, 63.06; H, 4.41; Cl, 10.34; N, 8.17; O,
4.67; S, 9.35. Found: C, 63.03; H, 4.39; S, 9.34.
2-(3,4-Dimethylphenoxy)-N-(4-(3-fluorophenyl)thiazol-2-
yl)acetamide (9i)
1
Isolated yield 79 %, (yellow solid), m.p. 158–159 °C, H
NMR (400 MHz, DMSO-d6) d (ppm): 2.12 (s, 3H), 2.17 (s,
3H), 4.81 (s, 2H), 6.66–0.00 (m, 1H), 6.79 (d, J = 2.48 Hz,
1H), 7.03 (d, J = 8.32 Hz, 1H), 7.14–7.19 (m, 1H),
7.45–7.50 (m, 1H), 7.69–7.72 (m, 1H), 7.76 (d,
J = 7.84 Hz, 1H), 7.79 (s, 1H), 12.50 (s, 1H). 13C NMR
(100 MHz, DMSO-d6) d (ppm):18.87(C-25), 20.09(C-24),
66.54(C-15), 110.22(C-5), 111.81(C-18), 112.59(C-12),
112.82(C-22) 115.08(C-10), 122.18(C-14), 129.25(C-20),
130.64(C-19), 131.22(C-13), 137.01(C-9), 137.09(C-21),
148.08(C-4), 157.92(C-17), 161.84(C-11), 164.26(C-2),
167.83(C-7). IR(KBr, cm-1): 3,469 (N–H) 1,697 (C=O),
1,352 (C–O–C), 1,249 (C–N). MS calcd. For
C19H17FN2O2S 356.41 Found: 357.0 (M?). Anal. Calc. for
C19H17FN2O2S C, 64.03; H, 4.81; F, 5.33; N, 7.86; O, 8.98;
S, 9.00. Found: C, 64.01; H, 4.79; S, 9.01.
N-(4-(3-Chlorophenyl)thiazol-2-yl)-2-(3-
methoxyphenyl)acetamide (9l)
1
Isolated yield 81 %, (white solid), m.p. 166–168 °C, H
NMR (400 MHz, DMSO-d6) d (ppm): 3.75 (s, 3H), 3.77 (s,
2H), 6.83–6.86 (m, 1H), 6.91 (s, 1H), 6.92–6.93 (m, 1H),
7.25 (t, J = 7.96 Hz, 1H), 7.37–7.39 (m, 1H), 7.47 (t,
J = 7.80 Hz, 1H), 7.78 (s, 1H), 7.85–7.88 (m, 1H), 7.96 (t,
J = 1.76 Hz, 1H). 13C NMR (100 MHz, DMSO-d6) d
(ppm):42.20(C-15), 55.48(C-24), 110.08(C-5), 112.70(C-
17, C-19), 115.56(C-21), 121.91(C-14), 124.64(C-10),
125.84(C-12), 127.97(C-20), 129.91(C-13), 131.14(C-9),
134.05(C-11), 136.74(C-16), 147.68(C-4), 158.53(C-17),
158.73(C-2), 169.91(C-7). IR(KBr, cm-1): 3,406 (N–H),
1,651 (C=O), 1,321 (C–N). MS calcd. For C18H15ClN2O2S
358.84. Found: 359.0 (M?). Anal. Calc. for C18H15ClN2
O2S C, 60.25; H, 4.21; Cl, 9.88; N, 7.81; O, 8.92; S, 8.94.
Found: C, 60.23; H, 4.20; S, 8.91.
N-(4-(3-Chlorophenyl)thiazol-2-yl)-2-p-tolylacetamide (9j)
1
Isolated yield 76 %, (white solid), m.p. 194–196 °C, H
NMR (400 MHz, DMSO-d6) d (ppm): 2.26 (s, 3H), 3.73 (s,
2H), 7.13 (d, J = 7.84 Hz, 2H), 7.22 (d, J = 7.88 Hz, 2H),
7.37 (d, J = 7.96 Hz, 1H), 7.45 (t, J = 7.84 Hz, 1H), 7.76
(s, 1H), 7.85 (d, J = 7.72 Hz, 1H), 7.95 (s, 1H), 12.50 (s,
1H). 13C NMR (100 MHz, DMSO-d6) d (ppm):21.11
N-(4-(3-Chlorophenyl)thiazol-2-yl)-2-(3,4-
dimethylphenoxy)acetamide (9m)
Isolated yield 85 %, (pale yellow solid), m.p. 156–157 °C,
1H NMR (400 MHz, DMSO-d6) d (ppm): 2.13 (s, 3H), 2.18
(s, 3H), 4.82 (s, 2H), 6.68 (d, J = 5.96 Hz, 1H), 6.79 (s,
1H), 7.03 (d, J = 8.00 Hz, 1H), 7.38 (d, J = 7.32 Hz, 1H),
7.46 (t, J = 7.68 Hz, 1H), 7.81 (s, 1H), 7.87 (d,
J = 7.36 Hz, 1H), 7.96 (s, 1H), 12.49 (s, 1H). 13C NMR
(100 MHz, DMSO-d6) d (ppm):18.47(C-25), 19.68(CC-
24), 66.08(C-15), 109.89(C-5), 111.35(C-18), 116.06
(C-22), 124.25(C-14), 125.44(C-10), 127.61(C-12),
(C-23),
41.78(C-15),
110.04(C-5),
124.63(C-14),
125.84(C-10), 127.96(C-12), 129.44(C-18, C-20), 129.57
(C-17, C-21), 131.13(C-13), 132.27(C-16), 134.05(C-9),
136.38(C-11), 136.76(C-19), 147.66(C-4), 158.57(C-2),
170.19(C-7). IR(KBr, cm-1): 3,448 (N–H), 1,649 (C=O),
1,325 (C–N). MS calcd. For C18H15ClN2OS 342.84.
Found: 343.2. Anal. Calc. for C18H15ClN2OS C, 63.06; H,
123