Abstract
Thionyl chloride efficiently and selectively promoted the deacylation of N-arylacetamides and 2-chloro-N-arylacetamides, under anhydrous conditions, without effecting the ester group, aminosulfonyl group, or benzyloxyamide group. This method, which has been successfully applied to a variety of substrates including different N-arylacetamides and 2-chloro-N-arylacetamides, has the attractive advantages of inexpensive reagents, satisfactory selectivity, excellent yields, short reaction time, and convenient workup. This new method can probably be used to selectively deacylate between aromatic amides and alkyl amides.
Similar content being viewed by others
References
J. Adrian, H. Font, J.M. Diserens, F. Sanchez-Baeza, M.P. Marco, J. Agric. Food Chem. 57(2), 385–394 (2009)
A. Ashnagar, N.G. Naseri, F. Koraei, Int. J. Chem. Sci. 5(3), 1321–1331 (2007)
P.K. Suryadevara, S. Olepu, J.W. Lockman, J. Ohkanda, M. Karimi, C.L.M.J. Verlinde, J.M. Kraus, J. Schoepe, W.C. Van Voorhis, A.D. Hamilton, F.S. Buckner, M.H. Gelb, J. Med. Chem. 52(12), 3703–3715 (2009)
L. Wan, X.B. Wang, S.M. Wang, S.Q. Li, Q. Li, R. Tian, M.J. Li, J. Phys. Org. Chem. 22(4), 331–336 (2009)
J.H. Hutchinson, Y.W. Li, J.M. Arruda, C. Baccei, G. Bain, C. Chapman, L. Correa, J. Darlington, C.D. King, C. Lee, D. Lorrain, P. Prodanovich, H.J. Rong, A. Santini, N. Stock, P. Prasit, J.F. Evans, J. Med. Chem. 52(19), 5803–5815 (2009)
L.Y. Safina, G.A. Selivanova, K.Y. Koltunov, V.D. Shteingarts, Tetrahedron Lett. 50(37), 5245–5247 (2009)
T.S. Wang, M.W. Ledeboer, J.P. Duffy, A.C. Pierce, H.J. Zuccola, E. Block, D. Shlyakter, J.K. Hogan, Y.L. Bennani, Bioorg. Med. Chem. Lett. 20(1), 153–156 (2010)
V. Bavetsias, E.A. Henderson, E. McDonald, Tetrahedron 63(7), 1537–1543 (2007)
K.P. Bhusari, N.D. Amnerkar, P.B. Khedekar, M.K. Kale, R.P. Bhole, Asian J. Res. Chem. 1(2), 53–58 (2008)
B. Schmidt, R. Berger, F. Hoelter, Org. Biomol. Chem. 8(6), 1406–1414 (2010)
D.L. Parker, D.F. Meng, R.W. Ratcliffe, R.R. Wilkening, D.M. Sperbeck, M.L. Greenlee, L.F. Colwell, S. Lambert, E.T. Birzin, K. Frisch, S.P. Rohrer, S. Nilsson, A.G. Thorsell, M.L. Hammond, Bioorg. Med. Chem. Lett. 16(17), 4652–4656 (2006)
C.M. Wassvik, A.G. Holmen, R. Draheim, P.B. Artursson, A.S. Christel, J. Med. Chem. 51(10), 3035–3039 (2008)
R. Hosseinzadeh, M. Tajbakhsh, M. Mohadjerani, E. Ghorbani, Chin. J. Chem. 26(11), 2120–2124 (2008)
B. Karimi, H. Behzadnia. Synlett. 13, 2019–2023 (2010)
C. Ramalingan, Y.T. Park, J. Org. Chem. 72(12), 4536–4538 (2007)
C.B. Aakeroey, I. Hussain, S. Forbes, J. Desper, Aust. J. Chem. 62(8), 899–908 (2009)
R. Saez, M.D. Otero, B. Batanero, F. Barba. J. Chem. Res. 9, 492–494 (2008)
G.Z. Fang, J.M. Pan, Chem. Anal. 50(5), 925–934 (2005)
X.J. Wang, Q. Yang, F. Liu, Q.D. You, Synth. Commun. 38(7), 1028–1035 (2008)
D. Kalyani, A.R. Dick, W.Q. Anani, M.S. Sanford, Tetrahedron 62(49), 11483–11498 (2006)
G. Felix, J. Dunogues, R. Calas, Angew. Chem. 1(5), 430–432 (1979)
H. Kano, H. Nishimura, K. Nakajima, K. Ogata. U.S. Patent 2888455, 19590526
DK Patent 63165, 19450212
W.K. Su, Y. Zhang, J.J. Li, P. Li, Org. Prep. Proc. Int. 40(6), 543–550 (2008)
G. Brahmachari, S. Laskar, S. Sarkar, J. Chem. Res. 34(5), 288–295 (2010)
CH Patent 233766, 19441116
F.W. Bergstrom, C.H. Horning, J. Org. Chem. 11, 334–340 (1946)
R.D. Gano, R.L. McKee, J.W. Ager, J. Am. Chem. Soc. 74, 3176–3177 (1952)
S.C. Bunce, J.B. Cloke, J. Am. Chem. Soc. 76, 2244–2248 (1954)
K. Yamamoto, S. Udagawa, Nippon Nogei Kagaku Kaishi. 26, 589–594 (1953)
M.U. Ali, M.G. Paranjpe, Indian J. Chem. Sect. B. 23B(6), 573–574 (1984)
G. Singh, J. Srivastava, Indian J. Chem. Technol. 11(6), 834–842 (2004)
C.G. Haining, R.G. Johnston, K.A. Scott, J. Pharm. Pharmacol. 12, 641–647 (1960)
B. Bobranski, Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 277, 75–86 (1939)
H.C. Brown, B.C.S. Rao, J. Am. Chem. Soc. 82, 681–686 (1960)
S.O. Li, C.P. Chang, Huaxue Xuebao. 23, 99 (1957)
S.H. Bhosale, M.S. Rode, S.S. Basagare, A.A. Gawai, M.S. Bhosale, K.R. Mahadik, S.S. Kadam, Indian J. Heterocycl. Chem. 15(3), 267–270 (2006)
A.D. Desai, K.H. Chikhalia, Eur. J. Chem. 2(6), 15–20 (2005)
V.Y. Svetkin, A.N. Minlibaeva, Zh. Obshch, Khim. 30, 2579–2581 (1960)
E. Epstein, D. Kaminsky, J. Am. Chem. Soc. 79, 5814–5817 (1957)
R.B. Patel, K.H. Chikhalia, Indian J. Chem. Sect. B. 45B(8), 1871–1879 (2006)
A.J. Harte, T. Gunnlaugsson, Tetrahedron Lett. 47(35), 6321–6324 (2006)
S. Imamura, Y. Nishikawa, T. Ichikawa, T. Hattori, Y. Matsushita, S. Hashiguchi, N. Kanzaki, Y. Iizawa, M. Baba, Y. Sugihara, Bioorg. Med. Chem. 13(2), 397–416 (2004)
U.P. Basu, J. Sikdar, J. Indian Chem. Soc. 24, 466–468 (1947)
Z.W. Lou, L. Zhou, C.F. Xiao, Y. Ye, F.B. Zeng, K.X. Huang, Med. Chem. Res. 16(7/9), 380–391 (2008)
A.H. El-Masry, Pak. J. Sci. Ind. Res. 45(2), 69–75 (2002)
W.F. Bruce, J. Seifter, U.S. Patent 2568141, 19510918
S. Darvesh, R.S. McDonald, A. Penwell, S. Conrad, K.V. Darvesh, D. Mataija, G. Gomez, A. Caines, R. Walsh, E. Martin, Bioorg. Med. Chem. 13(1), 211–222 (2004)
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Wang, GB., Wang, LF., Li, CZ. et al. A facile and efficient method for the selective deacylation of N-arylacetamides and 2-chloro-N-arylacetamides catalyzed by SOCl2 . Res Chem Intermed 38, 77–89 (2012). https://doi.org/10.1007/s11164-011-0327-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-011-0327-6