Synthesis of Novel 1-[(2,6-Dichloro-4-trifluoromethyl)phenyl]-3-aryl-1H-pyrazole-4-carbaldehydes
Abstract
:1. Introduction
2. Results and Discussion
X-ray diffraction
Compound | C15 H10 Cl3 F3 N2 |
---|---|
Color | Colorless |
Formula weight | 381.60 |
Crystal system | Monoclinic |
Temperature,° | 25(298K) |
Cell constants | |
a (Å) | 16.8770(7) |
b (Å) | 8.0054(8) |
c (Å) | 24.119(2) |
α (˚) | 90 |
β (˚) | 99.654(2) |
γ (˚) | 90 |
Volume (Å3) | 3212.5(4) |
Formula units | 8 |
Calculated density (g/cm-3) | 1.578 |
F(000) | 1536 |
Absorption coefficient, mμ-3 | 0.599 |
Limiting indices | -20<=h<=16, -7<=k<=9, -27<=l<=28 |
Reflections collected / unique | 8110 / 2841 [R(int) = 0.0402] |
Absorption correction | Semi-empirical from equivalents |
Max. and min. transmission | 0.9370 and 0.8314 |
Refinement method | Full-matrix least-squares on F2 |
Data / restraints / parameters | 2841 / 0 / 208 |
Goodness-of-fit on F2 | 1.015 |
Final R indices | R1 = 0.1641, wR2 = 0.5152 |
Largest diff. peak and hole (e Å-3) | 0.869 and -0.919 |
Entry | Ar | Products(6) | Yield(%) a |
1 | C6H5 | 6a | 89 |
2 | 4-ClC6H4 | 6b | 88 |
3 | 3-ClC6H4 | 6c | 83 |
4 | 4-BrC6H4 | 6d | 86 |
5 | 3-BrC6H4 | 6e | 82 |
6 | 4-MeOC6H4 | 6f | 83 |
7 | 4-CF3C6H4 | 6g | 86 |
8 | 4-NO2C6H4 | 6h | 85 |
9 | 6i | 81 |
3. Experimental
3.1. General
3.2. Synthesis of (2,6-Dichloro-4-trifluoromethyl)phenylhydrazine (3)
3.3. General procedure for synthesis of N-(2,6-Dichloro-4-trifluoromethyl)phenyl-N’-(1-phenyl-ethylidene) hydrazines 5a-i
3.4. General procedure for synthesis of 1-[(2,6-dichloro-4-trifluoromethyl)phenyl]-3-aryl-1H-pyrazole-4- carbaldehydes 6a-i
4. Conclusions
Acknowledgements
- Sample Availability: Samples of the compounds 6a-i are available from the authors.
References and Notes
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- CCDC 685556 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge, CB2 1EZ, UK; E-Mail: [email protected].
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Hu, H.; Ge, C.; Ding, L.; Zhang, A. Synthesis of Novel 1-[(2,6-Dichloro-4-trifluoromethyl)phenyl]-3-aryl-1H-pyrazole-4-carbaldehydes. Molecules 2010, 15, 7472-7481. https://doi.org/10.3390/molecules15107472
Hu H, Ge C, Ding L, Zhang A. Synthesis of Novel 1-[(2,6-Dichloro-4-trifluoromethyl)phenyl]-3-aryl-1H-pyrazole-4-carbaldehydes. Molecules. 2010; 15(10):7472-7481. https://doi.org/10.3390/molecules15107472
Chicago/Turabian StyleHu, Huanan, Changhua Ge, Lisheng Ding, and Anjiang Zhang. 2010. "Synthesis of Novel 1-[(2,6-Dichloro-4-trifluoromethyl)phenyl]-3-aryl-1H-pyrazole-4-carbaldehydes" Molecules 15, no. 10: 7472-7481. https://doi.org/10.3390/molecules15107472