1804
A. R. Katritzky et al.
PAPER
(5) Evans, T. W.; Dehn, W. M. J. Am. Chem. Soc. 1930, 52,
J = 7.8 Hz, 2 H), 7.41 (d, J = 7.8 Hz, 2 H) 8.32 (s, 1 H), 10.27 (s, 1
H), 10.37 (s, 1 H).
3647.
(6) (a) Bailey, N.; Dean, A. W.; Judd, D. B.; Middlemiss, D.;
Storer, R.; Watson, S. P. Bioorg. Med. Chem. Lett. 1996, 6,
1409. (b) Kearney, P. C.; Fernandez, M.; Flygare, J. A. J.
Org. Chem. 1998, 63, 196. (c) Stadlwieser, J.; Ellmerer-
Muller, E. P.; Tako, A.; Maslouh, N.; Bannwarth, W. Angew.
Chem. Int. Ed. 1998, 37, 1402. (d) Boga, C.; Forlani, L.;
Silvestroni, C.; Corradi, A. B.; Sgarabotto, P. J. Chem. Soc.,
Perkin Trans. 1 1999, 1363. (e) Majcen-Le Marechal, A.;
Le Grel, P.; Robert, A.; Biškup, J.; Ferk, V.; Toplak, R.
M.; Djafri, A.; Vanthuyne, N.; Roussel, C. Arkivoc 2002, x,
(7) Patil, D. G.; Chedekel, M. R. J. Org. Chem. 1984, 49, 997.
usa.org.
(9) Fu, M.; Fernandez, M.; Smith, M. L.; Flygare, J. A. Org.
Lett. 1999, 1, 1351.
13C NMR: d = 13.6, 20.1, 30.5, 45.3, 120.0, 124.5, 129.1, 136.7,
152.2, 179.3.
Anal. Calcd for C12H17N3OS: C, 57.34; H, 6.82. Found: C, 56.98; H,
6.90.
1-[({[Diethylaminocarbothioyl]amino}carbonyl)amino]-4-
methoxybenzene (6h)
Colorless microcrystals from EtOAc–CH2Cl2 (62%); mp 104–
105 °C.
1H NMR: d = 1.26 (t, J = 7.2 Hz, 6 H), 3.67–3.88 (m, 7 H), 6.86 (d,
J = 8.7 Hz, 2 H), 7.43 (d, J = 9.0 Hz, 2 H), 8.16 (s, 1 H), 12.25 (s, 1
H).
13C NMR: d = 12.3, 45.8, 55.4, 114.0, 122.3, 130.3, 151.7, 156.3,
176.0.
Anal. Calcd for C13H19N3O2S: N, 14.93. Found: N, 14.59.
(10) Jahn, U.; Andersch, J.; Schroth, W. Synthesis 1997, 573.
(11) Winckelmann, I.; Larsen, E. H. Synthesis 1986, 1041.
(12) Gopalsamy, A.; Yang, H. J. Comb. Chem. 2000, 2, 378.
(13) Yang, R.-Y.; Kaplan, A. P. Tetrahedron Lett. 2001, 42,
4433.
(14) (a) Schroeder, D. C. Chem. Rev. 1955, 55, 181.
(b) Barluenga, J.; Rubio, E.; Tomas, M. In Comprehensive
Organic Functional Group Transformations, Vol. 6;
Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.;
Pergamon: Oxford, 1995, 569.
N-(Morpholinocarbothioyl)propanamide (6i)
Colorless microcrystals from MeOH–CH2Cl2 (56%); mp 116–
117 °C (Lit.61 mp 154 °C).
1H NMR: d = 1.18 (t, J = 7.5 Hz, 3 H), 2.37 (q, J = 7.5 Hz, 2 H),
3.46–4.50 (m, 8 H), 8.02 (br s, 1 H).
13C NMR: d = 8.9, 30.3, 51.9, 66.2, 169.6, 178.8.
Anal. Calcd for C8H14N2O2S: C, 47.50; H, 6.98; N, 13.85. Found:
C, 47.62; H, 6.98; N, 13.80.
(15) Loev, B.; Bender, P. E.; Bowman, H.; Helt, A.; McLean, R.;
Jen, T. J. Med. Chem. 1972, 15, 1024.
(16) Kurzer, F. Org. Synth. Coll. Vol. 4; Wiley: New York, 1963,
180.
N,N-Diethyl-N¢-isonicotinoylthiourea (6j)
Colorless microcrystals from EtOAc–hexanes (35%); mp 108–
109 °C.
(17) (a) Douglass, I. B.; Dains, F. B. J. Am. Chem. Soc. 1934, 56,
1408. (b) Frank, R. L.; Smith, P. V. Org. Synth. Coll. Vol. III
1955, 735. (c) Rasmussen, C. R.; Villani, F. J. Jr.; Weaner,
L. E.; Reynolds, B. E.; Hood, A. R.; Hecker, L. R.; Nortey,
S. O.; Hanslin, A.; Costanzo, M. J.; Powell, E. T.; Molinari,
A. J. Synthesis 1988, 456.
1H NMR: d = 1.26–1.38 (m, 6 H), 3.50–3.70 (m, 2 H), 4.00–4.02 (m,
2 H), 7.70 (br s, 2 H), 8.76–8.78 (m, 2 H), 9.1 (br s, 1 H).
13C NMR: d = 11.3, 13.3, 47.5, 47.8, 121.4, 139.8, 150.6, 162.3,
178.6.
Anal. Calcd for C11H15N3OS: C, 55.67; H, 6.37. Found: C, 55.38; H,
6.53.
(18) Neville, R. G.; McGee, J. J. Org. Synth. Coll. Vol. V 1973,
801.
(19) Erickson, J. G. J. Org. Chem. 1956, 21, 483.
(20) (a) Moore, M. L.; Crossley, F. S. Org. Synth. Coll. Vol. III
1955, 617. (b) Fülöp, F.; Martinek, T.; Bernáth, G. Arkivoc
(21) Bernstein, J.; Yale, H. L.; Losee, K.; Holsing, M.; Martins,
J.; Lott, W. A. J. Am. Chem. Soc. 1951, 73, 906.
(22) Koketsu, M.; Fukuta, Y.; Ishihara, H. Tetrahedron Lett.
2001, 42, 6333.
N,N-Diethyl-N¢-(2-furylcarbonyl)thiourea (6k)
Light-brown microcrystals from CH2Cl2 (80%); mp 74–75 °C
(Lit.63 mp 78–79 °C).
1H NMR: d = 1.20–1.45 (m, 6 H), 3.64 (br s, 2 H), 4.01 (br s, 2 H),
6.56 (dd, J = 3.3, 1.8 Hz, 1 H), 7.24 (d, J = 3.3 Hz, 1 H), 7.54 (d, 2
H, J = 0.9 Hz).
13C NMR: d = 11.3, 13.1, 47.8, 112.7, 117.0, 145.2, 146.2, 153.7,
178.1.
(23) Cressman, H. W. J. Org. Synth. Coll. Vol. III 1955, 609.
(24) Kristian, P.; Kutschy, P.; Dzurilla, M. Collect. Czech. Chem.
Commun. 1979, 44, 1324.
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Synthesis 2004, No. 11, 1799–1805 © Thieme Stuttgart · New York