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M. D. Crozet et al.
1,2-Dimethyl-5-nitro-4-(tosylmethyl)-1H-imidazole (8b). Yellow solid,
1
mp 2008C (propan-2-ol). H NMR (CDCl3): d 2.44 (s, 3H), 2.47 (s, 3H),
3.85 (s, 3H), 4.80 (s, 2H), 7.32 (d, J ¼ 8.1 Hz, 2H), 7.73 (d, J ¼ 8.1 Hz,
2H). 13C NMR (CDCl3): d 14.1, 21.7, 34.1, 56.1, 128.3, 129.8, 132.8,
136.4, 145.0, 148.6. Anal. calcd. for C13H15N3O4S: C, 50.47; H, 4.89; N,
13.58. Found: C, 50.45; H, 5.01; N, 13.60.
4-(4-Chlorophenylsulfonyl)methyl-1,2-dimethyl-5-nitro-1H-imidazole (8c).
1
Yellow solid, mp 1878C (propan-2-ol). H NMR (CDCl3): d 2.46 (s, 3H),
3.87 (s, 3H), 4.83 (s, 2H), 7.50 (d, J ¼ 8.6 Hz, 2H), 7.79 (d, J ¼ 8.6 Hz, 2H).
13C NMR (CDCl3): d 14.1, 34.1, 56.1, 129.5, 129.8, 132.4, 137.7, 140.8,
148.7. Anal. calcd. for C12H12ClN3O4S: C, 43.71; H, 3.67; N, 12.74. Found:
C, 43.67; H, 3.70; N, 12.95.
4-(4-Bromophenylsulfonyl)methyl-1,2-dimethyl-5-nitro-1H-imidazole (8d).
1
Yellow solid, mp 2038C (propan-1-ol). H NMR (CDCl3): d 2.47 (s, 3H),
3.87 (s, 3H), 4.83 (s, 2H), 7.67 (d, J ¼ 8.9 Hz, 2H), 7.73 (d, J ¼ 8.9 Hz, 2H).
13C NMR (CDCl3): d 14.1, 34.2, 56.0, 129.4, 129.9, 132.3, 132.5, 138.3,
148.7. Anal. calcd. for C12H12BrN3O4S: C, 38.52; H, 3.23; N, 11.23. Found:
C, 38.68; H, 3.26; N, 11.06.
2-[2-Methyl-5-nitro-4-(phenylsulfonyl)methyl-1H-imidazol-1-yl]ethanol (9a).
Yellow solid, mp 1908C (propan-2-ol). 1H NMR (DMSO-d6): d 2.37 (s, 3H), 3.57
(t, J ¼ 5.2 Hz, 2H), 4.27 (q, J ¼ 5.2 Hz, 2H), 4.85 (s, 2H), 7.53–7.72 (m, 5H). 13
C
NMR (DMSO-d6): d 14.2, 49.0, 55.7, 59.9, 128.1, 129.4, 133.1, 134.3, 138.8,
150.2. Anal. calcd. for C13H15N3O5S: C, 47.99; H, 4.65; N, 12.92. Found:
C, 48.34; H, 4.69; N, 12.88.
2-[2-Methyl-5-nitro-4-(tosylmethyl)-1H-imidazol-1-yl]ethanol (9b). Yellow
1
solid, mp 1898C (propan-2-ol). H NMR (DMSO-d6): d 2.40 (s, 3H), 2.42
(s, 3H), 3.61 (t, J ¼ 5.2 Hz, 2H), 4.31 (t, J ¼ 5.2 Hz, 2H), 4.85 (s, 2H), 7.39
(d, J ¼ 8.2 Hz, 2H), 7.57 (d, J ¼ 8.2 Hz, 2H). 13C NMR (DMSO-d6): d 14.2,
21.2, 48.9, 55.8, 59.9, 128.1, 129.8, 133.1, 136.1, 136.6, 144.8, 150.1. Anal.
calcd. for C14H17N3O5S: C, 49.55; H, 5.05; N, 12.38. Found: C, 49.85;
H, 5.15; N, 12.25.
2-[4-(4-Chlorophenylsulfonyl)methyl-2-methyl-5-nitro-1H-imidazol-1-yl]eth
1
anol (9c). Yellow solid, mp 1828C (propan-2-ol). H NMR (DMSO-d6):
d 2.41 (s, 3H), 3.60–3.65 (m, 2H), 4.31 (t, J ¼ 5.1 Hz, 2H), 4.93 (s, 2H),
5.05 (broad s, 1H), 7.59–7.78 (m, 4H). 13C NMR (DMSO-d6): d 14.2, 48.9,
55.6, 59.8, 129.5, 130.2, 132.9, 136.6, 137.7, 139.3, 150.2. Anal. calcd. for
C13H14ClN3O5S: C, 43.40; H, 3.92; N, 11.68. Found: C, 43.40; H, 3.99;
N, 11.20.