Rai et al.
7.67 (br, s, 1H), 7.77 (m, 1H) 7. 80–7.82 (m, 2H), 8.5 (br, s, 1H). MS:
m ⁄ z = 365.0 (M+).
(2-{[4-(4-bromophenyl)-1,3-thiazol-2-yl]methoxy}-
5-chlorophenyl)(phenyl)methanone 4d
Yield 82%; m.p. 128.5–130.8 ꢀC; H-NMR (400 MHz, CDCl3): d 5.33
1
(s, 2H, OCH2), 7.04–7.01 (d, 1H), 7.27 (s, 1H), 7.37–7.48 (m, 4H),
7.49–7.61 (m, 3H), 7.69–7.72 (d, 2H), 7.84–7.87 (d, 2H); 13C-NMR
(100 MHz, CDCl3): d, 68.12, 114.04, 114.14, 114.60, 122.17, 127.15,
127.72, 128.48, 129.62, 129.78, 130.72, 131.62, 131.83, 132.96,
133.42, 137.19, 153.78, 154.02, 165.95, 194.41. MS: m ⁄ z = 486.0
(M+); IR (KBr) (mmax ⁄ cm): 755 (C–S–C), 1454, 1594 (C=N), 1658 (C=O),
3098 ⁄ cm (CH Aromatic); Anal. Calcd. for C23H15BrClNO2S: C, 56.98;
H, 3.12; N, 2.89. Found: C, 56.87; H, 3.25; N, 2.72.
2-[2-(4-bromobenzoyl)-4-chlorophenoxy]ethanethio-
amide 3g
Yield 73%; m.p. 182.5–183.7 ꢀC, H-NMR (300 MHz, CDCl3): d 5.1
(s, 2H, OCH2), 6.93–6.95 (d, 1H), 7.60–7.65 (m, 3H), 7.67 (br, s, 1H),
7.75 (m, 1H) 7. 78–7.81 (m, 2H), 8.6 (br, s, 1H). MS: m ⁄ z = 384.0
(M+).
1
General procedure for the synthesis of 2-[2-(aroyl-
aroxy)-methyl]-4-phenyl-1,3-thiazoles 4a–j
A mixture of 3a (5 g, 0.014 mol) and phenacyl bromide (3.3 g,
0.014 mol) in ethanol (50 mL) was refluxed for 8 h. Reaction mix-
ture was concentrated and purified by silica gel flash column chro-
matography with ethylacetate–hexane (1:9), to give 5.2 g of 4a in
76% yield.
(2-{[4-(4-chlorophenyl)-1,3-thiazol-2-yl]methoxy}-
5-methylphenyl)(phenyl)methanone 4e
Yield 70%; m.p. 137.1–138.2 ꢀC; H-NMR (400 MHz, CDCl3): d 2.3
1
(s, 3H, CH3), 5.5 (s, 2H, OCH2), 7.02–7.05 (d, 1H), 7.26–7.32 (m, 2H),
7.43–7.49 (m, 5H), 7.53–7.58 (m, 1H), 7.78–7.89 (m, 4H); 13C-NMR
(100 MHz, CDCl3): d 20.39, 68.05, 113.78, 128.31, 129.16, 130.37,
130.41, 130.45, 130.47, 130.48, 130.50, 130.53, 130.67, 131.45,
132.97, 137.93, 153.25, 153.85, 166.87, 196.28. MS: m ⁄ z = 420.2
(M+); IR (KBr) (mmax ⁄ cm): 776 (C–S–C), 1457, 1609 (C=N), 1651
(C=O), 3100 ⁄ cm (CH Aromatic); Anal. Calcd. for C24H18ClNO2S: C,
68.64; H, 4.32; N, 3.34. Found: C, 68.49; H, 4.54; N, 3.19.
(5-bromo-2-{[4-(4-chlorophenyl)-1,3-thiazol-2-yl]
methoxy}phenyl)(phenyl)methanone 4a
Yield 76%; m.p.132.2–133.1 ꢀC; 1H-NMR (400 MHz, CDCl3): d 5.3
(s, 2H, OCH2), 6.99–7.01 (d, 1H), 7.36–7.40 (m, 2H), 7.44–7.49 (m,
2H), 7.54–7.60 (m, 3H), 7.60–7.61 (m, 3H), 7.71–7.76 (d, 2H); 13C-
NMR (100 MHz, CDCl3): d 68.11, 114.01, 114.38, 114.60, 127.50,
128.54, 129.85, 131.19, 132.50, 132.58, 133.49, 134.05, 134.63,
137.24, 154.10, 154.36, 165.96, 194.37. MS: m ⁄ z = 486.0 (M+); IR
(KBr) (mmax ⁄ cm): 754, 1592 (C=N), 1447, 1659 (C=O), 3123 (CH Aro-
matic); Anal. Calcd. for C23H15BrClNO2S: C, 56.98; H, 3.12; N, 2.89.
Found: C, 56.88; H, 3.23; N, 2.90.
(2-{[4-(4-bromophenyl)-1,3-thiazol-2-yl]methoxy}-
5-methylphenyl)(phenyl)methanone 4f
1
Yield 76%; m.p. 139.8–140.9 ꢀC H-NMR (400 MHz, CDCl3): d 2.3 (s,
3H, CH3), 5.5 (s, 2H, OCH2), 7.02–7.05 (d, 1H), 7.26–7.32 (m, 2H),
7.43–7.49 (m, 5H), 7.53–7.58 (m, 1H), 7.78–7.89 (m, 4H); 13C-NMR
(100 MHz, CDCl3): d 20.39, 68.05, 113.78, 128.31, 129.16, 130.37,
130.38, 130.39, 130.40, 130.41, 130.43, 130.44, 130.48, 131.45,
132.97, 137.93, 153.25, 153.85, 166.87, 196.28. MS: m ⁄ z = 465.2
(M+); IR (KBr) (mmax ⁄ cm): 768 (C–S–C), 1450, 1620 (C=N), 1658 (C=O),
3098 ⁄ cm (CH Aromatic); Anal. Calcd. for C24H18BrNO2S: C, 62.07; H,
3.91; N, 3.02. Found: C, 61.95; H, 4.10; N, 2.90.
{5-bromo-2-[(4-phenyl-1,3-thiazol-2-yl)methoxy]
phenyl}(phenyl)methanone 4b
Yield 80%; m.p.134.4–139.5 ꢀC; 1H-NMR (400 MHz, CDCl3): d 5.3
(s, 2H, OCH2), 6.99–7.01 (d, 1H), 7.27 (s, 1H), 7.37–7.48 (m, 2H),
7.52–7.61 (m, 5H), 7.69–7.71 (m, 2H), 7.83–7.85 (m, 2H); 13C-NMR
(100 MHz, CDCl3): d 68.0, 114.05, 122.18, 127.72, 128.49, 129.78,
131.12, 132.43, 132.95, 133.42, 134.57, 137.18, 154.29, 165.89,
194.28. MS: m ⁄ z = 530.1 (M+); IR (KBr) (mmax ⁄ cm): 747, 1448, 1591
(C=N), 1665 (C=O), 3104 ⁄ cm (CH Aromatic); Anal. Calcd. for
C23H15Br2NO2S: C, 52.20; H, 2.86; N, 2.65. Found: C, 52.17; H, 2.95,
N, 2.55.
(5-chloro-2-{[4-(4-chlorophenyl)-1,3-thiazol-2-yl]
methoxy}phenyl)(4-chlorophenyl)methanone 4g
Yield 73%; m.p. 134.2–135.3 ꢀC; 1H-NMR (400 MHz, CDCl3): d d
5.5 (s, 2H, OCH2), 7.04–7.07 (d, 1H), 7.25–7.31 (m, 2H), 7.42–7.48
(m, 4H), 7.52–7.57 (m, 1H), 7.77–7.87 (m, 4H); 13C-NMR (100 MHz,
CDCl3): d 68.10, 113.77, 128.34, 129.05, 130.37, 130.38, 130.39,
130.40, 130.41, 130.43, 130.44, 130.48, 131.45, 132.97, 137.99,
153.23, 153.85, 166.86, 196.30. MS: m ⁄ z = 475.2 (M+); IR (KBr)
(mmax ⁄ cm): 760 (C–S–C), 1446, 1620 (C=N), 1648 (C=O), 3012 ⁄ cm
(CH Aromatic); Anal. Calcd. for C23H14Cl3NO2S: C, 58.18; H, 2.97; N,
2.95. Found: C, 57.96; H, 3.18; N, 2.80.
{5-chloro-2-[(4-phenyl-1,3-thiazol-2-yl)methoxy]
phenyl}(phenyl)methanone 4c
1
Yield 67%; m.p.138.3–139.6 ꢀC; H-NMR (400 MHz, CDCl3): d 5.32
(s, 2H, OCH2), 7.04–7.06 (d, 1H), 7.26–7.40 (m, 3H), 7.42–7.48 (m,
4H), 7.56–7.60 (m, 1H), 7.75–7.78 (m, 2H), 7.84–7.88 (m, 2H); 13C-
NMR (100 MHz, CDCl3): d, 68.18, 114.03, 114.20, 114.60, 127.20,
127.50, 128.56, 128.95, 129.68, 129.85, 130.77, 131.69, 132.59,
133.49, 134.01, 137.25, 153.86, 154.05, 165.97, 194.48. MS: m ⁄ z =
440.5 (M+); IR (KBr) (mmax ⁄ cm): 778 (C–S–C), 1499, 1595 (C=N),
1656 (C=O), 3099 ⁄ cm (CH Aromatic); Anal. Calcd. for C23H15Cl2NO2S:
C, 62.73; H, 3.43; N, 3.18. Found: C, 62.60; H, 3.62; N, 2.97.
(4-chlorophenyl)(5-methyl-2-{[4-(4-methylphenyl)-
1,3-thiazol-2-yl]methoxy}phenyl)methanone 4h
Yield 87%; m.p. 135.7–136.7 ꢀC; H-NMR (400 MHz, CDCl3): d 2.32–
2.35 (2s, 6H, 2CH3), 5.5 (s, 2H, OCH2), 7.02–7.05 (d, 1H), 7.26–7.32 (m,
2H), 7.43–7.49 (m, 4H), 7.53–7.58 (m, 2H), 7.78–7.89 (m, 3H); 13C-NMR
(100 MHz, CDCl3): d 20.39, 20.41, 68.11, 113.75, 128.36, 129.10,
1
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Chem Biol Drug Des 2010; 75: 400–406