EtOAc, 80% CHCl3) 0.88; δH (500 MHz, DMSO) 12.58 (1H, br s, N-H-O), 8.06 (2H, d, 8.5 Hz, CH(Ph)),
ACCEPTED MANUSCRIPT
7.58 – 7.55 (3H, m, CH(Ph); NCH), 7.29 (1H, d, 3.5 Hz, SCH), 1.33 (9H, s, CH3); δC (125.7 MHz, DMSO)
165.3, 159.2, 156.0, 138.1, 129.8, 128.5, 125.9, 114.2, 35.3, 31.3. IR (KBr ν (cm-1)) 3151 (NH), 1664 (CON),
1553 (thiazole ring); MS m/z (rel int.): 260 (12, M+), 161 (100), 146 (11), 118 (13), 91 (8).
4-Methyl-N-(thiazol-2-yl)benzamide (3d). Yield: 195.6 mg (90%), pale yellow powder, mp 213–214
°C; [Found: C, 60.59; H, 4.66; N, 12.70; C11H10N2OS requires C, 60.53; H, 4.62; N, 12.83%]; Rf (20%
EtOAc, 80% CHCl3) 0.70; δH (500 MHz, DMSO) 12.52 (1H, br s, N-H-O), 8.01 (2H, d, 6.2 Hz, CH(Ph)),
7.56 (1H, br s, NCH), 7.35 (2H, d, 6.2 Hz, CH(Ph)), 7.27 (1H, br s, SCH), 2.40 (3H, s, CH3); δC (125.7 MHz,
DMSO) 165.4, 159.2, 143.2, 138.1, 129.9, 129.6, 128.6, 114.2, 21.5. IR (KBr ν (cm-1)) 3150 (NH), 1665
(CON), 1539 (thiazole ring); MS m/z (rel int.): 218 (16, M+), 190 (7), 119 (100), 91 (46), 65 (19).
4-Methoxy-N-(thiazol-2-yl)benzamide (4d). Yield: 187.8 mg (80%), white powder, mp 214–215°C;
[Found: C, 56.49; H, 4.41; N, 11.74; C11H10N2O2S requires C, 56.40; H, 4.30; N, 11.96%]; Rf (20% EtOAc,
80% CHCl3) 0.56; δH (500 MHz, DMSO) 12.47 (1H, br s, N-H-O), 8.12 (2H, d, 8.9 Hz, CH(Ph)), 7.56 (1H,
d, 3.5 Hz, NCH), 7.26 (1H, d, 3.5 Hz, SCH), 7.08 (2H, d, 8.9 Hz, CH(Ph)), 3.86 (3H, s, CH3); δC (125.7
MHz, DMSO) 164.8, 163.1, 159.4, 138.0, 130.7, 124.7, 114.3, 114.1, 56.0. IR (KBr ν (cm-1)) 3145 (NH),
1672 (CON), 1543 (thiazole ring), 1255 and 1020 (C-O); MS m/z (rel int.): 234 (13, M+), 135 (100), 107
(10), 92 (13), 77 (17).
N-(Thiazol-2-yl)-[1,1’-biphenyl]-4-carboxamide (5d). Yield: 252.6 mg (90%), pale brown powder, mp
208–209 °C; [Found: C, 68.46; H, 4.20; N, 9.84; C16H12N2OS requires C, 68.55; H, 4.31; N, 9.99%]; Rf (20%
EtOAc, 80% CHCl3) 0.77; δH (500 MHz, DMSO) 12.71 (1H, br s, N-H-O), 8.21 (2H, d, 8.5 Hz, CH(Ph)),
7.87 (2H, d, 8.5 Hz, CH(Ph)), 7.79 (2H, d, 7.5 Hz, CH(Ph)), 7.59 (1H, d, 3.5 Hz, NCH), 7.53 (2H, t, 7.5 Hz,
CH(Ph)), 7.45 (1H, t, 7.5 Hz, CH(Ph)), 7.31 (1H, d, 3.5 Hz, SCH); δC (125.7 MHz, DMSO) 165.2, 159.2,
144.4, 139.4, 138.1, 131.4, 129.6, 129.3, 128.8, 127.4, 127.2, 114.3. IR (KBr ν (cm-1)) 3150 (NH), 1668
(CON), 1544 (thiazole ring); MS m/z (rel int.): 280 (15, M+), 181 (100), 153 (47).
4-Fluoro-N-(thiazol-2-yl)benzamide (6d). Yield: 203.6 mg (92%), white powder, mp 194–195°C;
[Found: C, 54.17; H, 3.04; N, 12.50; C10H7N2OSF requires C, 54.05; H, 3.17; N, 12.61%]; Rf (20% EtOAc,
80% CHCl3) 0.65; δH (500 MHz, DMSO) 12.68 (1H, br s, N-H-O), 8.19 (2H, dd, JH-H 8.9 Hz, JH-F 5.5 Hz,
CH(Ph)), 7.58 (1H, d, 3.6 Hz, NCH), 7.40 (2H, dd, JH-H 8.9 Hz, JH-F 8.9 Hz, CH(Ph)), 7.30 (1H, d, 3.6 Hz,
SCH); δF (470.4 MHz, DMSO): -107.20 (1F, br s, CF(Ph)); δC (125.7 MHz, DMSO) 165.1 (d, JC-F 250.3 Hz),
164.6, 159.2, 138.1, 131.5 (d, JC-F 9.5 Hz), 129.3, 116.1 (d, JC-F 22.0 Hz), 114.3. IR (KBr ν (cm-1)) 3150
19