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(s, 1 arom. C); 128.8, 127.7, 127.0 (3d, 5 arom. CH); 123.4, 109.5 (2s, C(4), C(5)); 48.1 (t, CH2); 9.2, 9.1 (2q,
.
2 Me). EI-MS: 218 (100, M ), 185 (43, [M SH] ), 127 (30, [M C7H7] ), 91 (79, C7H7 ). Anal. calc. for
C12H14N2S (218.32): C 66.02, H 6.46, N 12.83, S 14.69; found: C 65.91, H 6.83, N 13.07, S 14.80.
1-Cyclohexyl-4,5-dimethylimidazole-2(3H)-thione (9d): 200 mg (95%). Colorless crystals. M.p. 221 ± 2238
(EtOH). IR: 3040vs, 2920vs, 2820vs, 2660s, 1660s, 1510s, 1455s, 1420s, 1400s, 1380s, 1280s, 1250s, 1120m, 1020m,
1000m, 800s. 1H-NMR: 11.94 (br. s, NH); 4.86 (m, 1 H); 2.18, 2.06 (2s, 2 Me); 1.9 ± 1.5 (br. m, 10 H). 13C-NMR:
157.2 (s, CS); 121.1, 120.8 (2s, C(4), C(5)); 57.1 (d, CH); 30.6, 26.1, 25.4 (3t, 5 CH2); 10.6, 8.9 (2q, 2 Me). EI-
.
MS: 210 (54, M ), 128(100), 95(7). Anal. calc. for C11H18N2S (210.34): C 68.81, H 8.63, N 13.32, S 15.24; found:
C 68.67, H 8.75, N 13.35, S 15.35.
1-Methyl-4,5-diphenylimidazole-2(3H)-thione (9e): 210 mg (79%). Colorless crystals. M.p. 279 ± 2818
(EtOH). IR: 2980s, 2880s, 1600m, 1495s, 1450s, 1430s, 1400s, 1385s, 1280m, 1145m, 800s. 1H-NMR: 11.46
(br. s, NH); 7.5 ± 7.25 (m, 10 arom. H); 3.49 (s, Me). 13C-NMR: 159.2 (s, CS); 129.6, 128.5, 127.9 (3s, C(4),
.
C(5), 2 arom. C); 130.7, 129.3, 128.8, 128.6, 126.6 (5d, 10 arom. CH); 32.6 (q, Me). EI-MS: 266 (100, M ), 265
(100, [M 1] ), 233 (8, [M SH] ), 232(13), 207(20), 206(12), 193(15), 165(18), 133(18), 118(13),
104(10), 77(19). Anal. calc. for C16H14N2S (266.36): C 72.16, H 5.30, N 10.53, S 12.02; found: C 72.19, H 5.42,
N 10.54, S 11.93.
1-Ethyl-4,5-diphenylimidazole-2(3H)-thione (9f): 269 mg (96%). Colorless crystals. M.p. 292 ± 2948
(EtOH). IR: 3000s, 2880s, 1600m, 1510s, 1490vs, 1460s, 1405s, 1380m, 1260s, 1140m, 780s. 1H-NMR: 11.05
(br. s, NH); 7.5 ± 7.2 (m, 10 arom. H); 4.04 (q, MeCH2); 1.21 (t, MeCH2). 13C-NMR: 159.9 (s, CS); 130.9, 128.0,
126.4 (3s, C(4), C(5), 1 arom. C); 129.7, 129.3, 128.8 (3d, 10 arom. CH); 40.3 (t, CH2); 14.3 (q, Me). EI-MS: 280
.
(100, M ), 279 (33, [M 1] ), 252(35), 240(12), 193(31), 165(16), 104(13), 103(12), 77(14). Anal. calc. for
C17H16N2S (280.39): C 72.82, H 5.75, N 9.99, S 11.43; found: C 72.54, H 6.05, N 10.05, S 11.28.
1-Benzyl-4,5-diphenylimidazole-2(3H)-thione (9g): 325 mg (95%). Colorless crystals. M.p. 268 ± 2708
(CHCl3). IR: 3020s, 2900s, 1600m, 1490s, 1480s, 1460s, 1405s, 1240s, 1205s, 1195s, 1090m, 790s, 780s. 1H-NMR:
11.78 (br. s, NH); 7.45 ± 7.0 (m, 15 arom. H); 5.26 (s, CH2). 13C-NMR: 160.5 (br. s, CS); 131.1, 128.5, 127.8 (3s,
C(4), C(5), 3 arom. C); 129.5, 128.9, 128.7, 128.4, 128.0, 127.5, 127.4, 126.5 (8d, 15 arom. CH); 48.4 (t, CH2). EI-
.
MS: 343 (18, [M 1] ), 342 (75, M ), 309 (24, [M SH] ), 193(100), 178(50), 165(12), 91(49), 77(14).
Anal. calc. for C22H18N2S (342.46): C 77.16, H 5.30, N 8.18, S 9.36; found: C 77.00, H 4.99, N 8.16, S 9.16.
1-Cyclohexyl-4,5-diphenylimidazole-2(3H)-thione (9h): 318 mg (95%). Colorless crystals. M.p. 295 ± 2978
(EtOH; [32]: 316 ± 3178). 1H-NMR: 10.36 (br. s, NH); 7.5 ± 7.15 (m, 10 arom. H); 4.20 (m, 1 H); 1.8 ± 1.2
(m, 10 H).
4,5-Diphenyl-1-(2-phenylethyl)imidazole-2(3H)-thione (9i): 314 mg (88%). Colorless crystals. M.p. 261 ±
1
2638 (acetone). IR: 3000vs, 2890s, 1600m, 1500vs, 1460s, 1410s, 1370s, 1270s, 1180s, 790s, 780s. H-NMR: 10.10
(br. s, NH); 7.5 ± 7.4, 7.25 ± 7.15, 7.0 ± 6.95 (3m, 15 arom. H); 4.16, 3.00 (2t, 2 CH2). 13C-NMR: 154.0 (s, CS);
131.0, 126.6, 126.3 (3s, C(4), C(5), 3 arom. C); 129.7, 129.2, 128.9, 128.8, 128.6, 128.1 (6d, 15 arom. CH); 46.6,
.
34.6 (2t, 2 CH2). EI-MS: 356 (49, M ), 252 (100, [M PhCH2CH2] ), 193(9), 165(9), 104 (12, PhCH2CH2 ),
77(8). Anal. calc. for C23H20N2S (356.49): C 77.49, H 5.65, N 7.86, S 8.99; found: C 77.77, H 5.95, N 7.86, S 9.00.
1,5-Dimethyl-4-phenylimidazole-2(3H)-thione (9j): 192 mg (94%). Colorless crystals. M.p. 254 ± 2568
(acetone; [33]: 247 ± 2498). 1H-NMR: 11.43 (br. s, NH); 7.45 ± 7.25 (m, 5 arom. H); 3.60, 2.30 (2s, 2 Me).
1-Butyl-5-methyl-4-phenylimidazole-2(3H)-thione (9k): 160 mg (65%). Colorless crystals. M.p. 285 ± 2878
(CHCl3). IR: 3000vs, 2880vs, 1635m, 1600m, 1500vs, 1450s, 1410s, 1400s, 1370s, 1280s, 1250m, 1230m, 1190m,
1130s, 940m, 920m, 790s, 780s. 1H-NMR: 11.53 (br. s, NH); 7.45 ± 7.25 (m, 5 arom. H); 2.33 (s, Me); 4.07 (t, CH2);
1.76, 1.44 (2m, 2 CH2); 0.98 (t, MeCH2). 13C-NMR ((D6)DMSO): 159.7 (s, CS); 138.6, 122.4, 121.2 (3s, C(4),
C(5), 1 arom. C); 127.7, 125.8 (2d, 5 arom. CH); 42.4, 29.3, 18.5 (3t, 3 CH2); 12.7, 8.8 (2q, 2 Me). EI-MS: 246 (99,
.
M
), 213 (100, [M SH] ), 204(32), 190(66), 130(14), 115(10), 103(13), 77(9). Anal. calc. for C14H18N2S
(246.37): C 68.25, H 7.36, N 11.37, S 13.01; found: C 68.30, H 7.56, N 11.40, S 12.67.
Ethyl 4,5-Dihydro-1-phenyl-5-thioxo-1,2,4-[1H]triazole-3-carboxylate (11): Prepared according to the
General Procedure described for imidazole 3-oxides 1 using triazole N-oxide 10 and 5a. Yield: 209 mg
(84%). Colorless crystals. M.p. 196 ± 1988 (EtOH). IR: 2880s, 1740vs (CO), 1600w, 1505m, 1470s, 1420m,
1390s, 1285s, 1240m, 1200s, 1105m, 1030m, 1020m, 805m, 790m, 700m. 1H-NMR ((D6)DMSO): 8.0 ± 7.9, 7.55 ± 7.4
(2m, 5 arom. H); 4.50 (q, MeCH2); 1.44 (t, MeCH2). 13C-NMR ((D6)DMSO): 167.4 (s, CS); 155.5, 137.3
.
(2s, C(3), 1 arom. C); 128.7, 128.4, 124.4 (3d, 5 arom. CH); 62.3 (t, CH2); 13.8 (q, Me). EI-MS: 249 (100, M ),
220 (14, [M Et] ), 202(20), 175(34), 91(42), 77(23). Anal. calc. for C11H11N3O2S (249.29): C 53.00, H 4.45,
N 16.86, S 12.86; found: C 52.91, H 4.56, N 16.85, S 12.71.
4. ꢀOne-Potꢁ Procedure for the Synthesis of Imidazole-2(3H)-thione 9d. A soln. of 3d (220 mg, 0.65 mmol),
2a (200 mg, 2 mmol), and 5b (170 mg, 1 mmol) in abs. EtOH (5 ml) was heated under reflux. After 6 h, the