JCPT  Vol.1 No.3 , October 2011
(Z)-N-(3-(2-Chloro-4-nitrophenyl)-4-methylthiazol-2(3H)-ylidene) Pivalamide: Synthesis and Crystal Structure
ABSTRACT
Synthesis of the title compound was carried out by base-catalyzed cyclization of 1-pivaloyl-3-(2-chloro-4-nitrophenyl) thiourea with α-bromoacetone produced in situ. The structure was confirmed by the spectroscopic and elemental analysis and single crystal X-ray diffraction data. It crystallizes in the triclinic space group P-1 with unit cell dime sions a = 8.7137(10), b = 10.2010(14), c = 10.6593(13), α = 62.671(9), β = 82.701(10), γ = 79.762(10), V = 827.21(8) ų, Z = 2.

Cite this paper
nullA. Saeed and M. Bolte, "(Z)-N-(3-(2-Chloro-4-nitrophenyl)-4-methylthiazol-2(3H)-ylidene) Pivalamide: Synthesis and Crystal Structure," Journal of Crystallization Process and Technology, Vol. 1 No. 3, 2011, pp. 41-48. doi: 10.4236/jcpt.2011.13007.
References
[1]   A. Shehata, H. I. Elsubbagh, A. M. Abdelal, M. A. Elsher-beny and A. A. Alobaid, “Synthesis, Antitumor and Anti- HIV-1 Testing of Certain Thieno[2,3-d]Pyrimidine, Thieno [2,3-d]Imidazo[1,2-c] Pyrimidine and Thieno [2,3-d] [1,3] Thiazine Derivatives,” Medicinal Chemistry Research, Vol. 6, 1996, pp. 148-152.

[2]   T. K. Venkatachalan, E. A. Sudbeck, C. Mao and F. M. Uckun, “Anti-HIV Activity of Aromatic and Heterocyclic Thiazolyl Thiourea Compounds,” Bioorganic & Medicinal Chemistry Letters, Vol. 11, No. 4, 2001, pp. 523-527. doi:10.1016/S0960-894X(01)00011-7

[3]   C. G. Bonde and N. J. J. Gaikwad, “Synthesis and Pre-liminary Evaluation of Some Pyrazine Containing Thia-zolines and Thiazolidinones as Antimicrobial Agents,” Bioorganic & Medicinal Chemistry Letters, Vol. 12, No. 9, 2004, pp. 2151-1255. doi:10.1016/j.bmc.2004.02.024

[4]   S. Bondock, W. Khalifa and A. A. Fadda, “Synthesis and Antimicrobial Evaluation of Some New Thiazole, Thia-zolidinone and Thiazoline Derivatives Starting from 1-Chloro-3,4-dihydronaphthalene-2-carboxaldehyde,” Eu-ropean Journal of Medicinal Chemistry, Vol. 42, No. 7, 2007, pp. 17-21. doi:10.1016/j.ejmech.2006.12.025

[5]   S. Eckhardt, “Recent Progress in the Development of Anticancer Agents,” Current Medicinal Chemistry Anti-cancer Agents, Vol. 2, No. 3, 2002, pp. 419-423. doi:10.2174/1568011024606389

[6]   C. L. Lee and M. M. Sim, “Solid-Phase Combinatorial Synthesis of 5-Arylalkylidene Rhodanine,” Tetrahedron Letters, Vol. 41, No. 30, 2000, pp. 5729-5735. doi:10.1016/S0040-4039(00)00866-2

[7]   A. Arcadi, O. A. Attanasi, G. Giorgi, P. Filippone, E. Rossi and S. Santeusanio, “Pyrido[3,4-c]Thiazoles through Combined Palladium-Catalysed Coupling of 2-Sub-sti- tuted-5-acetyl-4-thiazolyltriflates with Alkynes Annula- tion Reactions,” Tetrahedron Letters, Vol. 44, No. 46, 2003, pp. 8391-88396. doi:10.1016/j.tetlet.2003.09.123

[8]   Y. T. H. Fahmy and A. A. Bekhit, “Synthesis of Some New Bis-Thiazoles as Possible Anticancer Agents,” De Pharmazie, Vol. 57, No. 12, 2002, pp. 800-807.

[9]   M.-H. Shih and F.-Y. Ke, “Syntheses and Evaluation of Antioxidant Activity of Sydnonyl Substituted Thiazo- li-dinone and Thiazoline Derivatives,” Bioorganic & Medi-cinal Chemistry Letters, Vol. 12, No. 17, 2004, pp. 4633-4643.doi:10.1016/j.bmc.2004.06.033

[10]   A. Manaka, T. Ishii, K. Takahashi and M. Sato, “2-Acy- limino-3-alkyl-3H-thiazoline Derivatives: One-Pot, three- Component Condensation Synthesis of Novel β-Turn Mimics,” Tetrahedron Letters, Vol. 46, No. 3, 2007, pp. 419. doi:10.1016/j.tetlet.2004.11.105

[11]   Y. Sanemitsu, S. Kawamura, J. Satoh, T. Katayama and S. Hashimoto, “Synthesis and Herbicidal Activity of 2- Acy-limino-3-phenyl-1,3-thiazolines-A New Family of Blea- ching Herbicides,” Journal of Pesticide Science, Vol. 31, No. 3, 2006, pp. 305-308. doi:10.1584/jpestics.31.305

[12]   S. Bae, H.-G. Hahn and K. D. Nam, “Solid-Phase Syn-thesis of Fungitoxic 2-Imino-1,3-thiazolines,” Journal of Combinatorial Chemistry, Vol. 7, No. 1, 2005, pp. 7-15. doi:10.1021/cc049854w

[13]   C. A. Bolos, K. T. Papazisis, A. H. Kortsaris, S. Voyatzi, D. Zambouli and D. A. Kyziakidis, “Antiproliferative Ac-tivity of Mixed-Ligand dien-Cu(II) Complexes with Thiazole, Thiazoline and imidazole Derivatives,” Journal of Inorganic Biochemistry, Vol. 88, No. 1, 2002, pp. 25-29. doi:10.1016/S0162-0134(01)00344-0

[14]   Y. Chen, Y. J. Zhao, “Synthesis and Characterization of Polyacrylonitrile-2-amino-2-thiazoline Resin and Its Sor- ption Behavior for Noble Metal Ions,” Reactive and Func- tional Polymers, Vol. 55, No. 1, 2003, pp. 89-94. doi:10.1016/S1381-5148(02)00218-3

[15]   M. Bouchekara, A. Djafri, N. Vanthyne and C. Roussel, “Atropisomerism in Some N,N-Diaryl-2-iminothiazoline Derivatives: Chiral Separation and Configurational Sta-bility,” ARKIVOC, Vol. 2002, No. 10, 2003, pp. 72-75.

[16]   A. Saeed, N. A. Al-Masoudi, A. A. Ahmed and C. Panne-couque, “New Substituted Thiazol-2-yliedene-benzamides and Their Reaction with 1-Aza-2-azoniaallene Salts. Syn- thesis and Anti-HIV Activity,” Zeitschrift für Naturfor-schung, Vol. 66b, 2011, pp. 512-520.

[17]   A. Saeed, U. Shaheen, A. Hameed and F. Kazmi, “Syn-thesis, Characterization and Antimicrobial Activity of Some Novel (Substituted Fluorobenzoylimino)-3-(Substi tuted fluorophenyl)-4-methyl-1,3-thiazolines,” Journal of Fluorine Chemistry, Vol. 131, No. 3, 2010, pp. 333-339. doi:10.1016/j.jfluchem.2009.11.005

[18]   X-Area, Area-Detector Control and Integration Software, Stoe & Cie, Darmstadt, Germany.

[19]   R. H. Blessing, “An Empirical Correction for Absorption Anisotropy,” Acta Crystallographica, Vol. A51, 1995, pp. 33-38.

[20]   A. L. Spek, “Single-Crystal Structure Validation with the Program PLATON,” Journal of Applied Crystallography, Vol. 36, No. 1, 2003, pp. 7-13. doi:10.1107/S0021889802022112

[21]   G. M. Sheldrick, “A Short History of SHELX,” Acta Cry- stallographica, Vol. A64, 2008, pp. 112-122.

[22]   A. Saeed and M. Parvez, “The Crystal Structure of 1-(4-Chlorophenyl)-3-(4-Methylbenzoyl) Thiourea,” Cen-tral European Journal of Chemistry, Vol. 3, No. 4, 2005, pp. 780-787. doi:10.2478/BF02475204

[23]   R.-S. Zeng, J,-P. Zou, S.-J. Zhi, J. Chen and Q. Shen, “Novel Synthesis of 1-Aroyl-3-Aryl-4-Substituted Imi- dazole-2-Thiones,” Organic Letters, Vol. 5, No. 10, 2003, pp. 1657-1659. doi:10.1021/ol030024l

[24]   X.-C. Wang, F. Wang, Z. J. Quan, M.-G. Wang and Z. Li, “An Efficient and Clean Synthesis of 1-Aroyl-3-aryl-4- substituted Imidazole-2-Thiones in Water,” Journal of Chemical Research, Vol. 2005, pp. 689-660.

[25]   A. Saeed and M. Parvez, “Synthesis and Crystal Structure of Some New 2-(4-Methylbenzoyl imino)-3-aryl-4-me- thyl-1,3-thiazolines,” Journal of Heterocyclic Chemistry, Vol. 43, No. 4, 2006, pp. 1027-1030. doi:10.1002/jhet.5570430431

[26]   C. B. Singh, S. Murru, V. Kavala and B. K. Patel, “It Is Thiazolidene-2-Imine” and Not Imidazole-2-Thione as the Reaction Product of 1-Benzoyl-3-Phenylthiourea with Br2/Enolizable Ketone,” Organic Letters, Vol. 8, No. 23, 2006, pp. 5397-5399. doi:10.1021/ol062371b

[27]   A. Saeed, S. Zaman and M. Bolte, “Synthesis, Crystal Structure of Some Novel 2-Aroylimino-3-Aryl-4-Phenyl- 1,3-Thiazolines,” Synthetic Communications, Vol. 38, 2008, pp. 2185-2199.

 
 
Top