4
Tetrahedron
(a) Coats, S. J.; Link, J. S.; Hlasta, D. J. Org. Lett. 2003, 5, 721-
724; (b) Jesberger, M.; Davis, T. P.; Barner, L. Synthesis 2003,
1929-1958.
7.
8. Raucher, S.; Klein, P. J. Org. Chem. 1981, 46, 3558-3559.
9. Charette, A. B.; Grenon, M. J. Org. Chem. 2003, 68, 5792-5794.
10. Priebbenow, D. L.; Bolm, C. Chem. Soc. Rev. 2013, 42, 7870-
7880.
11. (a) Yadav, A. K.; Srivastava, V. P.; Yadav, L. D. S. Synth.
Commun. 2013, 44, 408-416; (b) Xu, H.; Deng, H.; Li, Z.; Xiang,
H.; Zhou, X. Eur. J. Org. Chem 2013, 2013, 7054-7057.
12. Guntreddi, T.; Vanjari, R.; Singh, K. N. Org. Lett. 2014, 16, 3624-
3627.
13. (a) Schlatter, M. J. J. Am. Chem. Soc. 1942, 64, 2722-2722; (b)
Spychała, J. Tetrahedron 2000, 56, 7981-7986; (c) Mills, J. E.
Synthesis 1986, 482-484.
14. Becerra-Figueroa, L.; Ojeda-Porras, A.; Gamba-Sánchez, D. J.
Org. Chem. 2014, 79, 4544-4552.
15. General procedure for thioacylation of aliphatic amines
Amide (5.1 mmol) and amine (3.0 mmol) were dissolved or
suspended in toluene (3.0 mL), SbCl3 (34 mg, 0.15 mmol) was
added, and the mixture was refluxed until complete conversion (by
TLC) of the amine. The hot reaction mixture was filtered through
a pad of celite, concentrated and purified by flash
chromatography. N-butyl-thioacetamide (3) was purified by flash
chromatography with DCM. 366 mg of compound were isolated;
1
93 % yield. Yellow oil. H NMR (400 MHz, CDCl3) δ (ppm) 3.65
(dd, J = 12.9, 7.1 Hz, 2H), 2.56 (s, 3H), 1.64 (dd, J = 15.0, 7.5 Hz,
2H), 1.36 - 1.45 (m, 2H), 0.96 (t, J = 7.3 Hz, 3H); 13C NMR (100
MHz, CDCl3) δ (ppm) 200.7, 46.2, 34.3, 30.1, 20.1, 13.7. IR:
3293, 3067, 2955, 2927, 2869, 1636, 1547, 1452 cm-1. HRMS:
calcd for C6H14NS:132.0847; found: 132.0851.
16. (a) Okuda, T.; Hashimoto, Y.; Terao, H.; Yamada, K.; Ichiba, S. J.
Mol. Struct. 1991, 245, 103-109; (b) Bryant, R.; James, S. C.;
Jeffery, J. C.; Norman, N. C.; Orpen, A. G.; Weckenmann, U.
Dalton Trans. 2000, 4007-4009.
17. General procedure for thioacylation of aromatic amines
Amide (5.1 mmol) was dissolved in toluene (1.0 mL), SbCl3 (34
mg, 0.15 mmol) was added, and the mixture was heated until the
amide was completely dissolved, then a solution of amine (3.0
mmol) in toluene (2.0 mL) was added with a syringe pump (rate
0.2 mL/h) and the mixture refluxed until complete conversion (by
TLC) of the amine. The hot reaction mixture was filtered through
a
pad of celite, concentrated and purified by flash
chromatography. N-(4-methoxyphenyl)ethanethioamide (11) was
purified by flash chromatography with DCM/ Cyclohexane (9:1).
351 mg of compound were isolated; 65% yield. mp: 115-117°C 1H
NMR (400 MHz, CDCl3) δ (ppm) 8.72 (bs, 1H), 7.51 (d, J = 8.9
Hz, 2H), 7.09 (d, J = 8.8 Hz, 2H), 6.94 – 6.88 (m, 4H), 3.82 (d, J =
6.9 Hz, 6H), 2.72 (s, 3H), 2.45 (s, 3H); 13C NMR (100 MHz,
CDCl3) δ (ppm) 204.9, 200.4, 159.1, 158.2, 131.7, 131.0, 126.8,
125.8, 114.7, 114.1, 55.5, 55.4, 35.6, 29.8; IR: 3423, 3211, 3006,
1611, 1508, 1248 cm-1. MS (EI): 181 (31), 165 (27), 140 (50), 132
(31), 123 (37), 108 (100), 92 (15), 77 (12), 59 (13), 52 (14).
18. Yang, W.; Fu, H.; Song, Q.; Zhang, M.; Ding, Y. Organometallics
2010, 30, 77-83.
19. Han, A.; Ozturk, I. I.; Banti, C. N.; Kourkoumelis, N.; Manoli, M.;
Tasiopoulos, A. J.; Owczarzak, A. M.; Kubicki, M.; Hadjikakou,
S. K. Polyhedron 2014, 79, 151-160.