3674
J. LI ET AL.
2H, PhH), 7.63 (s, 1H, NH); 13C NMR (DMSO-d6, 100 MHz): 36.1, 43.4, 55.3,
112.6, 127.0, 131.0, 155.5, 161.5; IR (KBr) nmax: 3225, 1741, 1655 cmꢁ1
.
1-Benzoylimidazolidin-2-one 3b. White crystal; mp: 167.3–169.1 ꢀC (lit.[15]
1
169–171 ꢀC); MS (EI): m=z (%) 190 (52), 105 (100), 77 (29); H NMR (DMSO-d6,
400 MHz): dH 3.39 (t, J ¼ 7.6 Hz, 2H, CH2), 3.91 (t, J ¼ 7.6 Hz, 2H, CH2), 7.37
(t, J ¼ 7.2 Hz, 2H, PhH), 7.45–7.52 (m, 3H, PhH), 7.64 (s, 1H, NH); 13C NMR
(DMSO-d6, 100 MHz): 36.1, 43.0, 127.3, 128.4, 130.6, 135.3, 155.2, 169.4; IR
(KBr) nmax: 3425, 1727, 1665 cmꢁ1
.
1-(4-Nitrobenzoyl)imidazolidin-2-one 3c. Yellow crystal; mp: 227.3–
1
229.4 ꢀC; MS (EI): m=z (%) 235 (51), 207 (34), 150 (100); H NMR (DMSO-d6,
400 MHz): dH 3.42 (t, J ¼ 8.0 Hz, 2H, CH2), 3.95 (t, J ¼ 8.0 Hz, 2H, CH2), 7.72
(d, J ¼ 8.8 Hz, 2H, PhH), 7.80 (s, 1H, NH), 8.22 (d, J ¼ 8.8 Hz, 2H, PhH);
13C NMR (DMSO-d6, 100 MHz): 36.2, 42.5, 93.9, 122.6, 129.2, 141.8, 154.9,
167.4; IR (KBr) nmax: 3425, 1754, 1660 cmꢁ1
.
1-(3-Nitrobenzoyl)imidazolidin-2-one 3d. Yellow crystal; mp: 196.2–
197.6 ꢀC; MS (EI): m=z (%) 235 (21), 218 (34), 150 (100), 104 (22); 1H NMR
(DMSO-d6, 400 MHz): dH 3.43 (t, J ¼ 7.6 Hz, 2H, CH2), 3.95 (t, J ¼ 7.6 Hz, 2H,
CH2), 7.69 (t, J ¼ 8.0 Hz, 1H, PhH), 7.79 (s, 1H, NH), 7.93 (d, J ¼ 8.8 Hz, 1H,
PhH), 8.31 (s, 1H, PhH), 8.33 (d, J ¼ 8.0 Hz, 1H, PhH); 13C NMR (DMSO-d6,
100 MHz): 36.1, 42.7, 123.1, 125.0, 129.1, 134.6, 136.9, 146.7, 155.1, 166.9; Anal.
Calcd. for C10H9N3O4: C, 51.06; H, 3.83; N, 17.87. Found: C, 51.16; H, 3.85; N,
17.92; IR (KBr) nmax: 3425, 1754, 1674 cmꢁ1
.
1-(2-Methoxybenzoyl)imidazolidin-2-one 3e. White crystal; mp: 126–
128 ꢀC; MS (EI): m=z (%) 220 (21), 189 (40), 135 (100); 1H NMR (DMSO-d6,
400 MHz): dH 3.36 (t, J ¼ 8.0 Hz, 2H, CH2), 3.71 (s, 3H, CH3), 3.89 (t, J ¼ 8.0 Hz,
2H, CH2), 6.90–6.94 (m, 1H, PhH), 6.97–6.99 (m, 1H, PhH), 7.13–7.15 (m, 1H,
PhH), 7.32–7.37 (m, 1H, PhH), 7.51 (s, 1H, NH); 13C NMR (DMSO-d6,
100 MHz): 34.9, 42.1, 58.5, 111.0, 119.8, 126.4, 127.6, 130.4, 133.1, 154.6, 166.8;
Anal. Calcd. for C11H12N2O3: C, 60.00; H, 5.45; N, 12.72. Found: C, 59.75; H,
5.46; N, 12.51; IR (KBr) nmax: 3333, 1757, 1670 cmꢁ1
.
1-(2-Chlorobenzoyl)imidazolidin-2-one 3f. Yellow crystal; mp: 116.2–
118.9 ꢀC; MS (EI): m=z (%) 225 (7), 189 (100), 139 (34), 111 (21); 1H NMR
(DMSO-d6, 400 MHz): dH 3.41 (t, J ¼ 8.0 Hz, 2H, CH2), 3.94 (t, J ¼ 8.0 Hz, 2H,
CH2), 7.33–7.42 (m, 4H, PhH), 7.70 (s, 1H, NH); 13C NMR (DMSO-d6,
100 MHz): 35.9, 41.7, 126.7, 128.0, 128.6, 129.3, 130.2, 136.4, 154.3, 165.8; IR
(KBr) nmax: 3299, 1759, 1638 cmꢁ1
.
1-(2-Chloro-4-nitrobenzoyl)imidazolidin-2-one 3g. Yellow crystal; mp: 221–
223.2 ꢀC; MS (EI): m=z (%) 225 (7), 189 (100), 139 (34), 111 (21); 1H NMR (DMSO-
d6, 400 MHz): dH 3.45 (t, J ¼ 8.0 Hz, 2H, CH2), 3.98 (t, J ¼ 8.0 Hz, 2H, CH2), 7.68 (d,
J ¼ 8.4 Hz, 1H), 7.88 (s, 1H, NH), 8.20–8.23 (m, 1H, PhH), 8.31 (d, J ¼ 2.4 Hz, 1H,
PhH); 13C NMR (DMSO-d6, 100 MHz): 36.2, 41.5, 122.1, 123.7, 129.0, 130.3, 142.6,
147.9, 154.2, 164.1; IR (KBr) nmax: 3424, 1746, 1677 cmꢁ1
.