S. Cesarini et al. / Bioorg. Med. Chem. 16 (2008) 4173–4185
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1H, NH, exchangeable). Calcd for C16H16N2O3S: C,
60.74; H, 5.1; N, 8.85; S, 10.13. Found: C, 61.03; H,
5.17; N, 9.03; S, 10.19.
1H, NH, exchangeable). Calcd for C16H15ClN2O4S: C,
52.39; H, 4.12; N, 7.64; S, 8.74. Found: C, 52.50; H,
3.88; N, 7.53; S, 8.67.
6.1.2.9. O-[2-(3-Chlorophenyl)ethyl]N-(4-nitrophenyl)thio-
carbamate (9). Mp 137–138 ꢁC; yield: 98% from CH2Cl2/
6.1.2.15. O-[2-(4-Methylphenyl)ethyl]N-(4-nitrophenyl)
thiocarbamate (15). Mp 130–132 ꢁC; yield: 79% from
1
1
methanol. IR (KBr) cmꢀ1: 3264, 1552, 1336. H NMR
CH2Cl2/diethyl ether. IR (KBr) cmꢀ1: 3212. H NMR
(CDCl3) d: 3.12 (t, J = 6.6 Hz, 2H, CH2Ph), 4.85 (t,
J = 6.6 Hz, 2H, CH2O), 7.08–7.80 (m, 6H, arom. H),
7.98-8.37 (m, 2H, arom. H), 10.87 (br s, 1H, NH, exchange-
able). Calcd for C15H13ClN2O3S: C, 53.49; H, 3.89; N, 8.32;
S, 9.52. Found: C, 53.41; H, 4.02; N, 8.29; S, 9.55.
(CDCl3) d: 2.35 (s, 3H, CH3), 3.10 (t, J = 6.6 Hz, 2H,
CH2Ph), 4.85 (t, J = 6.6 Hz, 2H, CH2O), 7.00–7.64 (m,
6H, arom. H), 7.96–8.30 (m, 2H, arom. H), 9.01 (br s,
1H, NH, exchangeable). Calcd for C16H16N2O3S: C,
60.74; H, 5.1; N, 8.85; S, 10.13. Found: C, 60.73; H,
5.10; N, 8.87; S, 10.10.
6.1.2.10. O-[2-(3-Hydroxyphenyl)ethyl]N-(4-nitrophenyl)
thiocarbamate (10). Mp 143–145 ꢁC; yield: 97% from
CH2Cl2/methanol. IR (KBr) cmꢀ1: 3391, 3256, 1551,
6.1.2.16. O-[2-(4-Chlorophenyl)ethyl]N-(4-nitrophenyl)
thiocarbamate (16). Mp 151–153 ꢁC; yield: 98% from
CH2Cl2/methanol. IR (KBr) cmꢀ1: 3263, 1552, 1337.
1H NMR (CDCl3) d: 3.11 (t, J = 6.6 Hz, 2H, CH2Ph),
4.83 (t, J = 6.6 Hz, 2H, CH2O), 7.08–7.76 (m, 6H, arom.
H), 7.94–8.32 (m, Hz, 2H, arom. H), 10.43 (br s, 1H,
NH, exchangeable). Calcd for C15H13ClN2O3S: C,
53.49; H, 3.89; N, 8.32; S, 9.52. Found: C, 53.61; H,
4.19; N, 7.97; S, 9.50.
1
1335. H NMR (DMSO-d6) d: 2.93 (t, J = 6.6 Hz, 2H,
CH2Ph), 4.63 (t, J = 6.6 Hz, 2H, CH2O), 6.44–6.70 (m,
3H, arom. H), 6.92–7.10 (m, 1H, arom. H), 7.39–7.68
(m, 2H, arom. H), 7.96–8.16 (m, 2H, arom. H), 9.31
(br s, 1H, OH, exchangeable), 11.54 (s, 1H, NH,
exchangeable). Anal. Calcd for C15H14N2O4S: C, 56.59;
H, 4.43; N, 8.8; S, 10.07. Found: C, 56.57; H, 4.53;
N, 8.51; S, 10.08.
6.1.2.17. O-[2-(4-Bromophenyl)ethyl]N-(4-nitrophenyl)
thiocarbamate (17). Mp 145–146 ꢁC; yield: 96% from
CH2Cl2/methanol. IR (KBr) cmꢀ1: 3256, 1552, 1337.
1H NMR (DMSO-d6) d: 3.12 (t, J = 6.6 Hz, 2H,
CH2Ph), 4.78 (t, J = 6.6 Hz, 2H, CH2O), 7.16–7.90 (m,
6H, arom. H), 8.05–8.38 (m, 2H, arom. H), 11.73 (br
s, 1H, NH, exchangeable). Calcd for C15H13BrN2O3S:
C, 47.26; H, 3.44; N, 7.35; S, 8.41. Found: C, 47.32;
H, 3.69; N, 7.10; S, 8.38.
6.1.2.11. O-[2-(3-Methoxyphenyl)ethyl]N-(4-chloro-
phenyl)thiocarbamate (11). Mp 84–86 ꢁC; yield: 41%
from diethyl ether/methanol. IR (KBr) cmꢀ1: 3208,
2965. 1H NMR (CDCl3) d: 3.03 (t, J = 6.6 Hz, 2H,
CH2Ph), 3.77 (s, 3H, CH3), 4.79 (t, J = 6.6 Hz, 2H,
CH2O), 6.63–7.46 (m, 8H, arom. H), 8.85 (br s, 1H,
NH, exchangeable). Anal. Calcd for C16H16ClNO2S:
C, 59.72; H, 5.01; N, 4.35; S, 9.96. Found: C, 59.61;
H, 4.99; N, 4.12; S, 9.95.
6.1.2.18. O-[2-(4-Hydroxyphenyl)ethyl]N-(4-nitro-
phenyl)thiocarbamate (18). Mp 195–197 ꢁC; yield:
99% from CH2Cl2/methanol. IR (KBr) cmꢀ1: 3459,
3267, 1550, 1334. 1H NMR (DMSO-d6) d: 2.89 (t,
J = 6.6 Hz, 2H, CH2Ph), 4.59 (t, J = 6.6 Hz, 2H,
CH2O), 6.47–6.69 (m, 2H, arom. H), 6.87–7.07 (m,
2H, arom. H), 7.34–7.70 (m, 2H, arom. H), 7.93–
8.12 (m, 2H, arom. H), 9.22 (s, 1H, OH, exchange-
able), 11.54 (s, 1H, NH, exchangeable). Anal. Calcd
for C15H14N2O4S: C, 56.59; H, 4.43; N, 8.8; S,
10.07. Found: C, 56.56; H, 4.60; N, 8.77; S, 10.06.
6.1.2.12. O-[2-(3-Methoxyphenyl)ethyl]N-(4-nitrophenyl)
thiocarbamate (12). Mp 135–136 ꢁC; yield: 98% from
CH2Cl2/methanol. IR (KBr) cmꢀ1: 3272, 2921, 1551,
1
1336. H NMR (DMSO-d6) d: 2.99 (t, J = 6.6 Hz, 2H,
CH2Ph), 3.63 (s, 3H, CH3), 4.66 (t, J = 6.6 Hz, 2H,
CH2O), 6.68–6.87 (m, 3H, arom. H), 7.0–7.22 (m, 1H,
arom. H), 7.44–7.64 (m, 2H, arom. H), 8.00–8.12 (m, 1H,
arom. H), 11.55 (s, 1H, NH, exchangeable). Calcd for
C16H16N2O4S: C, 57.82; H, 4.85; N, 8.43; S, 9.65. Found:
C, 57.81; H, 5.13; N, 8.14; S, 9.86.
6.1.2.13. O-[2-(3-Methoxyphenyl)ethyl]N-(3,4-dichlo-
rophenyl)thiocarbamate (13). Mp 60–62 ꢁC; yield: 75%
from diethyl ether/ethanol. IR (KBr) cmꢀ1: 3192,
2924. 1H NMR (CDCl3) d: 3.05 (t, J = 6.6 Hz, 2H,
CH2Ph), 3.77 (s, 3H, CH3), 4.80 (t, J = 6.6 Hz, 2H,
CH2O), 6.60–7.55 (m, 7H, arom. H), 8.73 (br s, 1H,
NH, exchangeable). Calcd for C16H15Cl2NO2S: C,
53.94; H, 4.24; N, 3.93; S, 9.00. Found: C, 54.10; H,
4.55; N, 3.83; S, 9.22.
6.1.2.19. O-[2-(4-Methoxyphenyl)ethyl]N-(4-nitro-
phenyl)thiocarbamate (19). Mp 145–146 ꢁC; yield:
77% from CH2Cl2/methanol. IR (KBr) cmꢀ1: 3264,
1
1553, 1335. H NMR (CDCl3) d: 3.09 (t, J = 6.6 Hz,
2H, CH2Ph), 3.83 (s, 3H, CH3), 4.85 (t, J = 6.6 Hz,
2H, CH2O), 6.78–7.58 (m, 6H, arom. H), 8.07–8.34
(m, 2H, arom. H), 8.85 (br s, 1H, NH, exchangeable).
C16H16N2O4S: C, 57.82; H, 4.85; N, 8.43; S, 9.65.
Found: C, 57.89; H, 4.95; N, 8.41; S, 9.51.
6.1.2.14. O-[2-(3-Methoxyphenyl)ethyl]N-(4-chloro-3-
nitrophenyl)thiocarbamate (14). Mp 51–53 ꢁC; yield: 22%
6.1.2.20. ( ) O-(2-Methyl-2-phenylethyl)N-(4-chloro-
phenyl)thiocarbamate (20). Mp 68–69 ꢁC; yield: 58%
from diethyl ether/methanol. IR (KBr) cmꢀ1: 3220,
from diethyl ether/petroleum ether. IR (KBr) cmꢀ1
:
3353, 1538, 1343. 1H NMR (DMSO-d6) d: 2.86–3.04
(m, 2H, CH2Ph), 3.62 (s, 3H, CH3), 4.50–4.70 (m, 2H,
CH2O), 6.62–6.84 (m, 3H, arom. H), 7.04–7.19 (m,
2H, arom. H), 7.48–7.67 (m, 2H, arom. H), 11.44 (s,
3104, 2925. H NMR (CDCl3) d: 1.26 (d, J = 7.2 Hz,
1
3H, CH3), 3.10–3.30 (m, 1H, CH), 4.53–4.74 (m, 2H,
CH2O), 6.68–7.45 (m, 9H, arom. H), 8.76 (br s, 1H,
NH, exchangeable). Anal. Calcd for C16H16ClNOS: C,