Isoxazoline compound isomer and preparation method thereof
A technology of isoxazolines and compounds, applied in the field of organic synthesis
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[0032] In a specific embodiment of the present invention, a single crystal of any one isoxazoline compound isomer of the structure shown in the above formula (1), formula (2), formula (3) or formula (4) is also provided and its preparation method, the applicant has found through research that by utilizing the solubility characteristics of the compound isomers in different solvents and the apparent thermodynamic behavior of the crystal, a suitable solvent system can be selected to successfully obtain the above formula (1), The single crystal of the four isomers of the structure shown in formula (2), formula (3) or formula (4) specifically includes the following steps: dissolving the isomer compound in a solvent to form a solution, according to the crystal The solubility sets the solvent composition and crystallization temperature. As an example, the specific method is as follows: Weigh the solid structure shown in the formula (1), formula (2), formula (3) or formula (4) in a gl...
Embodiment 1
[0046] Example 1 Preparation of 5-(4-chlorophenyl)-2,3-dimethyl-3-(3-pyridyl)isoxazoline enantiomers
[0047] 5-(4-chlorophenyl)-2,3-dimethyl-3-(3-pyridyl)isoxazoline (prepared according to the method of Example 1 in ZL99113093.6), the 5-(4 -Chlorophenyl)-2,3-dimethyl-3-(3-pyridyl)isoxazoline is determined by HPLC under the following test conditions: test conditions, the chromatographic column is a Daicel chromatographic column CHIRALPAK IG0.46cm I.D.× 15cm L, the mobile phase is methanol-water mixture containing 0.02wt% acetic acid (the volume ratio of methanol to water is 80:20), the flow rate is 1.0ml / min, the column temperature is 35°C, the solvent is methanol, and the detection wavelength is 200nm. The HPLC spectrum is as figure 1 . Such as figure 1 , there are 4 peaks, which are the peak positions of the 4 isomers of 5-(4-chlorophenyl)-2,3-dimethyl-3-(3-pyridyl)isoxazoline, from the left To the right are recorded as: Isomer 1, Isomer 2, Isomer 3 and Isomer 4.
[004...
Embodiment 2
[0049] Embodiment 2 single crystal preparation
[0050] The powders of Isomer 1, Isomer 2, Isomer 3 and Isomer 4 prepared in Example 1 were weighed 0.3g in a glass vial, and 5mL of dichloromethane was added, and the sample was dissolved at room temperature. dissolve. Add 5 mL of dichloromethane and petroleum ether mixed solvent, the volume ratio is 1:1, crystallize at 25-30 ° C for 120 hours, the crystals precipitate and grow up, filter to obtain colorless crystals, and after drying, isomers 1 are obtained respectively , Isomer 2, Isomer 3 and Isomer 4 single crystals, the powders and single crystals of the four isomers were tested by DSC to characterize their thermodynamic behavior, the results are shown in Table 1-1. X-ray diffraction tests were carried out on the single crystals of the four isomers to obtain the diffraction spectra of isomer 1, isomer 2, isomer 3 and isomer 4 respectively, as shown in image 3 shown. Structural analysis was carried out on the single crys...
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