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

doi:10.3390/cryst2030967

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

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

Imtiaz Khan^1,* and Jonathan M. White²

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; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

Khan I, White JM. 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(3):967-973.

Chicago/Turabian Style

Khan, Imtiaz; White, Jonathan M. 2012. "Simple and Efficient One-Pot Synthesis, Spectroscopic Characterization and Crystal Structure of Methyl 5-(4-Chlorobenzoyloxy)-1-phenyl-1H-pyrazole-3-carboxylate." Crystals 2, no. 3: 967-973.

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