1,3-Disubstituted Imidazole-2-thiones
405
(125 MHz, CDCl3): d ¼ 162.3, 117.9, 116.6, 46.8, 35.1, 31.1, 19.8, 14.4,
13.7 ppm; FT-IR (neat): 3106, 3082, 2976, 2944, 1570, 1467, 1415, 1335,
1263, 1224, 1173 cm21; MS (ESI): m/z 185 ([MþH]þ); anal. calcd. for
C9H16N2S: C, 58.65; H, 8.75; N, 15.20. Found: C, 58.75; H, 8.79; N, 15.08.
1
1-iso-Butyl-3-ethylimidazole-2-thione (1e): Brown oil; H NMR (500 MHz,
CDCl3): d ¼ 6.71 (d, 1H, J ¼ 2.1 Hz), 6.67 (d, 1H, J ¼ 2.1 Hz), 4.11 (q, 2
H, J ¼ 5.4 Hz), 3.86 (d, 2H, J ¼ 7.4 Hz), 2.20–2.26 (m, 1H), 1.37 (t, 3H,
J ¼ 7.4 Hz), 0.95 (d, 6H, J ¼ 6.7 Hz) ppm; 13C NMR (125 MHz, CDCl3):
d ¼ 161.8, 117.8, 115.8, 55.3, 42.9, 29.9, 28.2, 20.1, 14.4 ppm; FT-IR
(neat): 3103, 3094, 2966, 2940, 1568, 1463, 1414, 1337, 1263, 1223,
1170 cm21; MS (ESI): m/z 185 ([MþH]þ); anal. calcd. for C9H16N2S:
C, 58.65; H, 8.75; N, 15.20. Found: C, 58.73; H, 8.80; N, 15.10.
1-n-Dodecyl-3-methylimidazole-2-thione (1f): Brown oil; 1H NMR (500 MHz,
CDCl3): d ¼ 6.72 (d, 1H, J ¼ 2.3 Hz), 6.70 (d, 1H, J ¼ 2.3 Hz), 4.03 (t, 2H,
J ¼ 7.4 Hz), 3.61 (s, 3H), 1.73–1.75 (m, 2H), 1.28–1.30 (m, 18H), 0.96 (t, 3
H, J ¼ 7.4 Hz) ppm; 13C NMR (125 MHz, CDCl3): d ¼ 162.5, 117.8, 116.6,
47.7, 35.4, 31.0, 28.5, 27.6, 27.2, 26.8, 26.5, 26.2, 25.8, 25.5, 19.8, 13.7 ppm;
FT-IR (neat): 3105, 3088, 2965, 2935, 1572, 1470, 1425, 1338, 1255, 1223,
1172 cm21; MS (ESI): m/z 283 ([MþH]þ); anal. calcd. for C16H30N2S: C,
68.03; H, 10.70; N, 9.92. Found: C, 68.25; H, 10.75; N, 9.87.
1
1-Benzyl-3-methylimidazole-2-thione (1g): Brown oil; H NMR (500 MHz,
CDCl3): d ¼ 7.29–7.33 (m, 5H), 6.66 (d, 1H, J ¼ 2.2 Hz), 6.56 (d, 1H,
J ¼ 2.2 Hz), 5.24 (s, 2H), 3.63 (s, 3H) ppm; 13C NMR (125 MHz,
CDCl3): d ¼ 162.4, 129.0, 128.4, 128.2, 118.1, 116.4, 51.5, 35.4 ppm; FT-
IR (neat): 3110, 3094, 2978, 2932, 1578, 1455, 1412, 1330, 1263, 1223,
1155 cm21; MS (ESI): m/z 205 ([MþH]þ).
1-Ethoxyacetyl-3-methylimidazole-2-thione (1h): Brown oil; 1H NMR
(500 MHz, CDCl3): d ¼ 6.78 (d, 1H, J ¼ 2.2 Hz), 6.74 (d, 1H, J ¼ 2.2 Hz),
4.86 (s, 2H), 4.25 (q, 2H, J ¼ 7.1 Hz), 3.61 (s, 3H) 1.30 (t, 3H, J ¼ 7.1 Hz)
ppm; 13C NMR (125 MHz, CDCl3): d ¼ 167.6, 163.8, 118.0, 117.4, 62.0,
48.8, 35.4, 14.2 ppm; FT-IR (neat): 3126, 2987, 2936, 1732, 1570, 1466,
1425, 1403, 1389, 1250, 1224, 1147, 1029 cm21; MS (ESI): m/z 201
([MþH]þ); anal. calcd. for C8H12N2O2S: C, 47.98; H, 6.04; N, 13.99.
Found: C, 47.95; H, 6.08; N, 13.86.
1-Propenyl-3-methylimidazole-2-thione (1i): Brown oil; 1H NMR (500 MHz,
CDCl3): d ¼ 6.71 (d, 1H, J ¼ 2.3 Hz), 6.70 (d, 1H, J ¼ 2.3 Hz), 5.90–5.95
(m, 1H), 5.27 (d, 2H, J ¼ 1.0 Hz), 4.68 (d, 2H, J ¼ 6.0 Hz), 3.63 (s, 3H)
ppm; 13C NMR (125 MHz, CDCl3): d ¼ 162.6, 132.1, 119.2, 117.9, 116.4,
50.4, 35.3 ppm; FT-IR (neat): 3159, 3110, 3091, 2979, 2925, 1644, 1568,
1459, 1398, 1344, 1242, 1210, 1157 cm21; MS (ESI): m/z 155 ([MþH]þ).