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CAS No. : | 21615-34-9 | MDL No. : | MFCD00000664 |
Formula : | C8H7ClO2 | Boiling Point : | - |
Linear Structure Formula : | CH3OC6H4C(O)Cl | InChI Key : | RZNHSEZOLFEFGB-UHFFFAOYSA-N |
M.W : | 170.59 | Pubchem ID : | 88969 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P261-P280-P305+P351+P338-P310 | UN#: | 3265 |
Hazard Statements: | H227-H314-H335 | Packing Group: | Ⅱ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Pyridine (4 mL) was added to 2- methoxybenzoylmethylammonium chloride (8a)/benzoylmethylammonium chloride (8b) salt (0.5 mmol) and stirred for 10 min at room temperature. To this mixture, above corresponding acid chloride was added slowly and stirred for 1 h under nitrogen atmosphere. After completion of the reaction, water (4 mL) was added, neutralized with 3 N HCl, and extracted with EtOAc (2 × 20 mL). The combined organic layer was washed with water (2 × 15 mL), brine (15 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. To this crude, acetic anhydride (3 mL) followed by conc. H2SO4 (0.1 mL) were added at room temperature and the mixture was stirred at 90C for 1 h. After completion of the reaction, cooled to room temperature, H2O (5 mL) was added. The mixture was neutralized with saturated aqueous NaHCO3 and extracted with EtOAc (2 × 25 mL). The combined organic layer was washed with water (2 × 15 mL), brine (15 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The crude was purified by column chromatography (EtOAc:hexane = 1:3) to afford the pure oxazole product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | General procedure: A mixture of dry dichloromethane (DCM, 2 mL) and dry pyridine (475 mg, 6 mmol, 3 molarequiv) was put into 25 mL round-bottom flask, closed with a stopper and cooled in a freezer forapproximately 15 min. A selected benzoyl chloride (2.4 mmol, 1.2 equiv) was diluted with dry DCM(5 mL) and added dropwise to the cooled (ice bath) pyridine/DCM mixture under stirring, and the mixture was stirred for additional 5 min in the closed flask. 2-Aminopyrazine (190 mg, 2 mmol,1 equiv) or 6-chloropyrazin-2-amine (259 mg, 2 mmol, 1 equiv) was dissolved in DCM (2 mL) andadded dropwise to the cooled reaction mixture over 10 min upon stirring. After additional 15 min,the reaction was removed from the ice bath and stirred at laboratory temperature. The progress ofreaction was monitored by TLC (silica plates, 33percent EtOAc in hexane). After 2 h, no significant furtherincrease in the spot of the product was observed, so the reaction was ended and worked-up.The reaction mixture was adsorbed on silica (4 g) by evaporating the solvents underreduced pressure. The mixture on silica was used for solid loading the flash chromatographypre-column. The separation used the following conditions: manually filled silica column (30 g),continuous gradient elution 0?50percent EtOAc in hexane, flow rate 35 mL/min, detection wavelength280 nm, monitoring wavelength 260 nm. Fractions containing pure product were combined andsolvents were evaporated under reduced pressure to yield solid product. If needed, the productswere recrystallized from hot EtOH, the crystallization was induced by cooling and addition of water.The products were isolated as white solids. In several cases, the final products were still contaminatedwith non-specified impurity of brown color. This impurity was easily removed by dispersing theproduct in small amount of hexane and immersion of a vertical piece of filtration paper into thisdispersion. The impurity was soluble in hexane and rose by capillary action to the filtration paper. |
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