HETEROCYCLES, Vol. 83, No. 5, 2011
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C17H16N2OS: C, 68.89; H, 5.44; N, 9.45. Found: C, 68.78; H, 5.53; N, 9.36.
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5-Benzyl-3-butyl-2-thioxoimidazolidin-4-one (4c). H NMR (CDCl3): δ = 9.16 (s, 1H), 7.30 (m, 5H),
5.30 (s, 1H), 3.48 (s, 2H), 3.02 (d, 2H, J = 6 Hz), 1.33 (m, 7H). IR (neat): 3446.12, 2925.06, 2856.66,
1680.08, 1457.49, 1391.21, 1201.59 cm-1. ESIMS, m/z: 263 (MH+). Anal. Calcd for C14H18N2OS: C,
64.09; H, 6.91; N, 10.68. Found: C, 64.21; H, 7.02; N, 10.59.
5-Isopropyl-3-phenyl-2-thioxoimidazolidin-4-one (4d). 1H NMR (CDCl3): δ = 7.38 (brs, 1H), 7.38 (m,
3H), 7.31 (m, 2H), 4.71 (d, 1H, J = 4 Hz), 2.38 (m, 1H), 1.15 (d, 3H, J = 7 Hz), 1.12 (3H, d, J = 7 Hz). IR
(neat): 3178.90, 2964.12, 1756.58, 1681.85, 1513.73, 1404.83, 1348.02, 1266.60, 1183.70, 759.03cm-1.
ESIMS, m/z: 235 (MH+). Anal. Calcd for C12H14N2OS: C, 61.51; H, 6.02; N, 11.96. Found: C, 61.58; H,
6.09; N, 11.85.
5-Isopropyl-2-thioxo-3-(m-tolyl)imidazolidin-4-one (4e). 1H NMR (CDCl3): δ = 7.50 (brs, 1H), 7.37 (m,
1H), 7.27 (s, 1H), 7.11 (m, 2H), 4.16 (d, 1H, J = 4 Hz), 2.40 (s, 3H), 2.33 (m, 1H), 1.22 (d, 3H, J = 6.8
Hz), 1.03–1.05 (d, 3H, J = 6.8 Hz). IR (neat): 3178.90, 2964.12, 1756.58, 1681.85, 1513.73, 1404.83,
1348.02, 1266.60, 1183.70, 759.03cm-1. ESIMS, m/z: 249 (MH+). Anal. Calcd for C13H16N2OS: C, 62.87;
H, 6.49; N, 11.28. Found: C, 62.95; H, 6.58; N, 11.21.
3-Butyl-5-isopropyl-2-thioxoimidazolidin-4-one (4f). 1H NMR (CDCl3): δ = 7.50 (brs, 1H), 7.26 (m,
2H), 7.27 (s, 1H), 7.11 (m, 2H), 4.16 (d, 1H, J = 4 Hz), 2.40 (s, 3H), 2.33 (m, 1H), 1.22 (d, 3H, J = 6.8
Hz), 1.03–1.05 (d, 3H, J = 6.8 Hz). IR (neat): 3441.09, 2966.12, 2864.59, 2510.67, 1681.83, 1464.29,
1200.35, 1135.50, 1060.51, 794.61cm-1. ESIMS, m/z: 215 (MH+). Anal. Calcd for C10H18N2OS: C, 56.04;
H, 8.47; N, 13.07. Found: C, 56.01; H, 8.56; N, 13.01.
5-Isobutyl-3-phenyl-2-thioxoimidazolidin-4-one (4g). 1H NMR (CDCl3): δ = 7.28 (m, 3H), 3.48 (s, 1H),
3.40 (m, 2H), 3.24 (m, 1H), 1.74 (m, 1H), 1.58 (m, 2H), 1.11 (d, 6H, J = 7 Hz). IR (neat): 3428.07,
2928.40, 1635.83, 1528.44, 1447.63, 1405.18, 1352.36, 1316.54, 1262.23, 756.86cm-1. ESIMS, m/z: 249
(MH+). Anal. Calcd for C13H16N2OS: C, 62.87; H, 6.49; N, 11.28. Found: C, 62.76; H, 6.56; N, 11.22.
5-Isobutyl-2-thioxo-3-(m-tolyl)imidazolidin-4-one (4h). 1H NMR (CDCl3): δ = 7.26 (m, 1H), 7.10 (m,
4H), 3.48 (m, 1H), 2.40 (s, 3H), 1.71 (m, 2H), 1.67 (m, 1H), 1.09 (d, 6H, J = 7 Hz). IR (neat): 3332.47,
2927.12, 2856.43, 1752.57, 1708.84, 1618.62, 1526.48, 1451.97, 1273.72, 1087.35cm-1. ESIMS, m/z: 263
(MH+). Anal. Calcd for C14H18N2OS: C, 64.09; H, 6.91; N, 10.68. Found: C, 64.08; H, 6.95; N, 10.58.
3-Butyl-5-isobutyl-2-thioxoimidazolidin-4-one (4i). 1H NMR (CDCl3): δ = 4.12 (t, 2H, J = 7 Hz), 3.73
(m, 1H), 2.02 (m, 2H), 1.62 (m, 1H), 1.43 (m, 2H), 1.33 (m, 2H), 1.25 (m, 3H), 0.97 (d, 6H, J = 7 Hz). IR