JOURNAL OF SULFUR CHEMISTRY
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117.8, 128.7, 129.4, 131.4, 138.2, 146.9, 157.9, 168.4, 170.4 ppm. C16H18N2O3S (318.39):
C, 60.36; H, 5.70; N, 8.80. Found: C, 60.44; H, 5.73; N, 8.78.
4.3.5. Ethyl 2-(2-acetamido-4-phenylthiazol-5-yl)acetate (4e)
1
Yellow oil; IR υ/cm−1 (KBr): 3162, 2973, 1735, 1546. H NMR (500 MHz, CDCl3):
δ = 1.29 (t, J = 7.0 Hz, 3H, CH3), 1.52 (s, 3H, CH3), 3.84 (s, 2H, CH2), 4.22 (q, J = 7.0 Hz,
2H, CH2), 7.39 (t, J = 7.0 Hz, 1H, Ar), 7.44 (d, J = 7.0 Hz, 2H, Ar), 7.58 (d, J = 7.0 Hz,
2H, Ar), 11.68 (bs, 1H, NH) ppm. 13C NMR (125 MHz, CDCl3): δ = 14.2, 21.9, 32.5, 61.5,
118.3, 128.4, 128.8, 129.5, 134.2, 146.8, 158.3, 168.5, 170.3 ppm. C15H16N2O3S (304.36):
C, 59.19; H, 5.30; N, 9.20. Found: C, 59.14; H, 5.29; N, 9.17.
4.3.6. Ethyl 2-(2-acetamido-4-(4-fluorophenyl)thiazol-5-yl)acetate (4f)
1
Yellow oil; IR υ/cm−1 (KBr): 3263, 2919, 1734, 1546. H NMR (500 MHz, CDCl3):
δ = 1.29 (t, J = 7.0 Hz, 3H, CH3), 1.93 (s, 3H, CH3), 3.79 (s, 2H, CH2), 4.22 (q, J = 7.0 Hz,
2H, CH2), 7.13 (d, J = 8.5 Hz, 2H, Ar), 7.55 (d, J = 8.5 Hz, 2H, Ar), 10.32 (bs, 1H, NH)
ppm. 13C NMR (125 MHz, CDCl3): δ = 14.1, 22.6, 39.4, 61.6, 115.6, 122.7, 127.2, 130.5,
142.7, 145.6, 150.7, 167.8, 176.5 ppm. C15H15FN2O3S (322.35): C, 55.89; H, 4.69; N, 8.69.
Found: C, 55.97; H, 4.70; N, 8.65.
4.3.7. N-(4-(4-chlorophenyl)-5-(2,2-diethoxy-6-hydroxy-4-oxo-1,2,3,
4-tetrahydropyrimidin-5-yl)thiazol-2-yl)acetamide (6a)
White solid; Mp: >320°C. IR υ/cm−1 (KBr): 3411, 3151, 2979, 1687, 1578. 1H
NMR (500 MHz, CDCl3): δ = 1.13 (t, J = 7.5 Hz,6H, CH3), 2.12 (s, 3H, CH3), 3.04
(q, J = 7.5 Hz, 2H, CH2), 3.06 (q, J = 7.5 Hz, 2H, CH2), 7.35 (d, J = 8.5 Hz, 2H, Ar-),
7.67 (d, J = 8.5 Hz, 2H, Ar), 8.90 (bs, 1H, OH), 10.01 (bs, 2H, NH), 11.96 (bs, 1H, NH)
ppm. 13C NMR (125 MHz, CDCl3): δ = 9.1, 22.9, 46.2, 80.3, 128.3, 129.2, 131.4, 135.7,
143.9, 151.4, 156.2, 161.3, 163.2, 168.5, 168.6 ppm. C19H21ClN4O5S (452.91): C, 50.39; H,
4.67; N, 12.37. Found: C, 50.48; H, 4.70; N, 12.35.
4.3.8. N-(5-(2,2-diethoxy-6-hydroxy-4-oxo-1,2,3,4-tetrahydropyrimidin-5-yl)-
4-(p-tolyl)thiazol-2-yl)acetamide (6b)
1
White solid; Mp: >320°C. IR υ/cm−1 (KBr): 3396, 3167, 2979, 1673, 1571. H NMR
(500 MHz, CDCl3): δ = 1.12 (t, J = 6.5 Hz, 6H, CH3), 2.09 (s, 3H, CH3), 2.24 (s, 3H,
CH3), 3.03 (q, J = 6.5 Hz, 4H, CH2), 7.04 (d, J = 7.5 Hz, 2H, Ar), 7.62 (d, J = 7.5 Hz, 2H,
Ar), 8.92 (bs, 1H, OH), 9.14 (bs, 2H, NH), 11.75 (bs, 1H, NH) ppm. 13C NMR (125 MHz,
CDCl3): δ = 9.1, 21.2, 22.9, 46.2, 78.3, 116.6, 124.0, 127.6, 128.5, 134.7, 135.3, 152.4, 154.9,
164.0, 168.0, 168.1 ppm. C20H24N4O5S (432.50): C, 55.54; H, 5.59; N, 12.95. Found: C,
55.48; H, 5.62; N, 12.89.
4.3.9. N-(4-(4-bromophenyl)-5-(2,2-diethoxy-6-hydroxy-4-oxo-1,2,3,
4-tetrahydropyrimidin-5-yl)thiazol-2-yl)acetamide (6c)
1
White solid; Mp: >320°C. IR υ/cm−1 (KBr): 3384, 3149, 2980, 1680, 1578. H NMR
(500 MHz, CDCl3): δ = 1.11 (t, J = 7.0 Hz, 6H, CH3), 2.09 (s, 3H, CH3), 3.03 (q,
J = 7.0 Hz, 4H, CH2), 7.43 (d, J = 8.5 Hz, 2H, Ar), 7.66 (d, J = 8.5 Hz, 2H, Ar), 8.92
(bs, 1H, OH), 9.33 (bs, 2H, NH), 11.82 (bs, 1H, NH) ppm. 13C NMR (125 MHz, CDCl3):
δ = 9.0, 22.9, 46.1, 78.7, 119.3, 125.4, 129.5, 130.8, 136.8, 137.4, 142.2, 152.3, 155.1, 163.8,