Simple and Efficient One-Pot Synthesis, Spectroscopic Characterization and Crystal Structure of Methyl 5-(4-Chlorobenzoyloxy)-1-phenyl-1H-pyrazole-3-carboxylate
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 yi...
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MDPI AG
2012-07-01
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| Series: | Crystals |
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| Online Access: | http://www.mdpi.com/2073-4352/2/3/967 |
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doaj-0ac4c06c9fb147d8a74c493e9617789a2020-11-24T23:04:37ZengMDPI AGCrystals2073-43522012-07-012396797310.3390/cryst2030967Simple and Efficient One-Pot Synthesis, Spectroscopic Characterization and Crystal Structure of Methyl 5-(4-Chlorobenzoyloxy)-1-phenyl-1H-pyrazole-3-carboxylateImtiaz KhanJonathan M. WhiteA 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.http://www.mdpi.com/2073-4352/2/3/967one-pot synthesispyrazoledimethyl acetylenedicarboxylatephenyl hydrazinebenzoyl chloridecrystal structure |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Imtiaz Khan Jonathan M. White |
| spellingShingle |
Imtiaz Khan Jonathan M. White Simple and Efficient One-Pot Synthesis, Spectroscopic Characterization and Crystal Structure of Methyl 5-(4-Chlorobenzoyloxy)-1-phenyl-1H-pyrazole-3-carboxylate Crystals one-pot synthesis pyrazole dimethyl acetylenedicarboxylate phenyl hydrazine benzoyl chloride crystal structure |
| author_facet |
Imtiaz Khan Jonathan M. White |
| author_sort |
Imtiaz Khan |
| title |
Simple and Efficient One-Pot Synthesis, Spectroscopic Characterization and Crystal Structure of Methyl 5-(4-Chlorobenzoyloxy)-1-phenyl-1H-pyrazole-3-carboxylate |
| title_short |
Simple and Efficient One-Pot Synthesis, Spectroscopic Characterization and Crystal Structure of Methyl 5-(4-Chlorobenzoyloxy)-1-phenyl-1H-pyrazole-3-carboxylate |
| title_full |
Simple and Efficient One-Pot Synthesis, Spectroscopic Characterization and Crystal Structure of Methyl 5-(4-Chlorobenzoyloxy)-1-phenyl-1H-pyrazole-3-carboxylate |
| title_fullStr |
Simple and Efficient One-Pot Synthesis, Spectroscopic Characterization and Crystal Structure of Methyl 5-(4-Chlorobenzoyloxy)-1-phenyl-1H-pyrazole-3-carboxylate |
| title_full_unstemmed |
Simple and Efficient One-Pot Synthesis, Spectroscopic Characterization and Crystal Structure of Methyl 5-(4-Chlorobenzoyloxy)-1-phenyl-1H-pyrazole-3-carboxylate |
| title_sort |
simple and efficient one-pot synthesis, spectroscopic characterization and crystal structure of methyl 5-(4-chlorobenzoyloxy)-1-phenyl-1h-pyrazole-3-carboxylate |
| publisher |
MDPI AG |
| series |
Crystals |
| issn |
2073-4352 |
| publishDate |
2012-07-01 |
| description |
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. |
| topic |
one-pot synthesis pyrazole dimethyl acetylenedicarboxylate phenyl hydrazine benzoyl chloride crystal structure |
| url |
http://www.mdpi.com/2073-4352/2/3/967 |
| work_keys_str_mv |
AT imtiazkhan simpleandefficientonepotsynthesisspectroscopiccharacterizationandcrystalstructureofmethyl54chlorobenzoyloxy1phenyl1hpyrazole3carboxylate AT jonathanmwhite simpleandefficientonepotsynthesisspectroscopiccharacterizationandcrystalstructureofmethyl54chlorobenzoyloxy1phenyl1hpyrazole3carboxylate |
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