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Crystals 2012, 2(3), 967-973; doi:10.3390/cryst2030967
Communication

Simple and Efficient One-Pot Synthesis, Spectroscopic Characterization and Crystal Structure of Methyl 5-(4-Chlorobenzoyloxy)-1-phenyl-1H-pyrazole-3-carboxylate

1,*  and 2
1 Department of Chemistry, Quaid-i-Azam University, Islamabad-45320, Pakistan 2 Bio-21 Institute, School of Chemistry, University of Melbourne, Parkville-3052, Australia
* Author to whom correspondence should be addressed.
Received: 22 May 2012 / Revised: 13 June 2012 / Accepted: 25 June 2012 / Published: 16 July 2012
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Abstract

A facile one-pot synthesis of methyl 5-(4-chlorobenzoyloxy)-1-phenyl-1H-pyrazole-3-carboxylate (4) is described. The title compound was efficiently synthesized by the reaction of phenyl hydrazine, dimethyl acetylenedicarboxylate and 4-chlorobenzoyl chloride in dichloromethane under reflux in good yield. The structure of the target compound was deduced by modern spectroscopic and analytical techniques and unequivocally confirmed by a single crystal X-ray diffraction analysis. The crystal of the title compound belongs to orthorhombic system, space group P 21 21 21 with cell parameters a = 6.6491(3) Å, b = 7.9627(6) Å, c = 30.621(5) Å, α = β = γ = 90° and Z = 4. The crystal packing of the compound (4) is stabilized by an offset π-stacking between the planar benzoyl-substituted diazole moieties.
Keywords: one-pot synthesis; pyrazole; dimethyl acetylenedicarboxylate; phenyl hydrazine; benzoyl chloride; crystal structure one-pot synthesis; pyrazole; dimethyl acetylenedicarboxylate; phenyl hydrazine; benzoyl chloride; crystal structure
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Khan, I.; White, J.M. Simple and Efficient One-Pot Synthesis, Spectroscopic Characterization and Crystal Structure of Methyl 5-(4-Chlorobenzoyloxy)-1-phenyl-1H-pyrazole-3-carboxylate. Crystals 2012, 2, 967-973.

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