Next Article in Journal
1,5-Diaminopentane As A Structure-Directing Agent for Zincophosphate Networks: Zn3(PO4)2(C5H14N2)2·3H2O and C5H16N2·Zn3(PO4)2(HPO4)·H2O
Previous Article in Journal
Preparation and Crystal Structure of Diaqua(μ-5,5'-bistetrazolato-κ4N1,N2,N5,N6)copper(II)
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
View Full-Text   |   Download PDF [210 KB, uploaded 16 July 2012]   |  

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 (CC BY 3.0).

Supplementary material

SciFeed

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Crystals EISSN 2073-4352 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert