Synthesis of Unsymmetrical Ureas and S-Thiocarbamates under Catalyst-free Conditions
7
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8.5 Hz, 2H), 7.39 (d, J = 6.4 Hz, 2H), 7.31–7.23 (m,
4H), 7.04 (t, J = 6.8 Hz, 1H), 2.33 (s, 3H).
S-(2-Naphtyl)-N-phenyl thiocarbamate (2d).
White solid; mp 170–173°C; 1H NMR (400 MHz,
DMSO-d6): δ 10.60 (s, 1H), 8.17 (d, J = 1.6 Hz, 1H),
7.99–7.97 (m, 3H), 7.63–7.56 (m, 3H), 7.52–7.50 (m,
2H), 7.31 (t, J = 7.4 Hz, 2H), 7.07 (t, J = 7.2 Hz,
1H). 13C NMR (100 MHz, DMSO-d6):119.55, 124.10,
125.97, 127.15, 127.69, 128.08, 128.26, 128.81,
129.41, 132.49, 133.17, 133.51, 135.26, 139.26,
163.34. Anal. Calcd. for C17H13NOS: (%) C 73.09,
H 4.69, N 5.01, S 11.48. Found: C 73.27, H 4.57, N
5.11, S 11.54.
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S-Benzyl-N-phenyl thiocarbamate (2e) [3i].
1
White solid; mp 93°C; H NMR (300 MHz, DMSO-
d6): δ 10.32 (s, 1H), 7.49 (d, J = 7.8 Hz, 2H),
7.37–7.20 (m, 7H), 7.04 (t, J = 7.3 Hz, 2H), 4.14 (s,
2H).
S-Cyclohexyl-N-phenyl thiocarbamate (2f) [3j].
White solid; mp 114–116°C; 1H NMR (300 MHz,
DMSO-d6): δ 10.15 (s, 1H), 7.47 (d, J = 8.5 Hz, 2H),
7.27 (t, J = 7.4 Hz, 2H), 7.02 (t, J = 7.1 Hz, 1H),
3.42–3.34 (m, 1H), 1.86–1.95 (m, 2H), 1.66–1.22 (m,
7H).
S-Octyl-N-phenyl thiocarbamate (2g) [3i].
White solid; mp 56–58°C (lit. 56.1–58.9°C); 1H NMR
(300 MHz, DMSO-d6): δ 10.22 (s, 1H), 4.49 (d, J =
8.5 Hz, 2H), 7.27 (t, J = 7.4 Hz, 2H), 7.02 (t, J =
7.1 Hz, 1H), 2.85 (t, J = 7.2 Hz, 2H), 1.51–1.60 (m,
2H), 1.23–1.35 (m, 10H), 0.83 (t, J = 6.6 Hz, 3H).
Acknowledgment
Research Council of University of Mazandaran.
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