Synthesis from N,Nꢀ-Disubstituted Thiorea Derivatives
1563
NMR: (DMSO-d6) δ = 1.26–1.95 (m, 10 H, cyclohexyl), 3.58 (m, 1H,
N CH), 7.03 (d, J = 8.9, 1H, Ar-H), 7.49 (d, J = 8.9, 1H, Ar-H), 7.70 (m,
1H, ArH), 7.89 (s, 1H, NH), 12.10 (s, 1H, OH), 13C NMR: (DMSO-d6): δ
= 23.9, 24.7, 31.6, 57.1, (cyclohexyl), 104.8, 110.5, 113.2, 132.9, 138.2,
146.9 (Ar-C), 167.8, 171.7 (C N and C O).
Calcd. for C14H16N2O2S (276.35): C, 60.85; H, 5.84; N, 10.14; S, 11.60.
Found: C, 60.81; H, 5.80; N, 10.12; S, 11.53.
3-Cyclohexyl-2-(1-naphthylimino)-1,3-thiazolidin-4-one (5)
To a mixture of 1b (10 mmol) and sodium ethoxide (prepared by dissolv-
ing 0.23 g of sodium metal in 20 mL of abs. ethanol), ethyl chloroacetate
(10 mmol) was added, and the reaction mixture was refluxed for 4 h,
diluted with water, and acidified. The solid thus separated was filtered
and crystallized from ethanol to give colorless crystals (76% yield); m.p.
= 210–212◦C. M+ = 324, base peak m/e = 163, IR (KBr): 1676 cm−1
1
(CO). H NMR: (DMSO-d6) δ = 1.15–1.93 (m, 10 H, cyclohexyl), 4.15
(m, 1H, N CH cyclohexyl), 4.39 (s, 2H, CH2), 6.99–7.91 (m, 7H, Ar-
H), 13C NMR: (DMSO-d6): δ = 24.2, 24.4, 31.9, 52.5, 61.9, (cyclohexyl,
CH2), 117.7, 121.4, 122.7, 122.9, 124.7, 125.4, 128.0, 128.4, 133.8, 134.9,
(Ar-C), 179.5, 181.1 (C N and C O).
Calcd. for C19H20N2OS (324.44): C, 70.34; H, 6.21; N, 8.63; S, 9.88.
Found: C, 70.29; H, 6.18; N, 8.58; S, 9.84.
1-Cyclohexyl-3-(1-naphthyl)-2-thioxoimidazolidin-4,5-dione (6)
To a mixture of 1b (10 mmol) and sodium ethoxide (prepared by dis-
solving 0.23 g of sodium metal in 20 mL of abs. ethanol), diethyl oxalate
(10 mmol) was added, and the reaction mixture was refluxed for 4 h,
diluted with water, and acidified with hydrochloric acid (3 mL, 60%).
The solid thus separated was filtered and crystallized from ethanol to
give colorless crystals (76% yield); m.p. = 115–117◦C. IR (KBr): 1447
(C S), 1660, 1670 cm−1 (2CO). 1H NMR: (DMSO-d6)δ = 1.06–1.88 (m,
10 H, cyclohexyl), 3.56 (m, 1H, N CH cyclohexyl), 7.34–8.54 (m, 7H,
Ar H), 13C NMR: (DMSO-d6): δ = 24.2, 25.2, 32.9, 47.6, (cyclohexyl),
115.7, 121.2, 121.6, 125.2, 125.3, 125.6, 125.8, 125.9, 126.0, 133.6, 153.3,
154.6, 181.8 (Ar C, 2C O, and C S).
Calcd. for C19H18N2O2S (338.42): C, 67.43; H, 5.36; N, 8.28; S, 9.47.
Found: C, 67.38; H, 5.35; N, 8.26; S, 9.46.
1-Cyclohexyl-3-(1-naphthyl)-2-thioxodihydropyrimidine-
4,6(1H,5H)-dione (7)
To a mixture of 1b (10 mmol) and sodium ethoxide (prepared by dissolv-
ing 0.23 g of sodium metal in 20 mL of abs. ethanol), diethyl malonate