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CAS No. : | 2516-40-7 | MDL No. : | MFCD02681887 |
Formula : | C7H4BrNS | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | DRLMMVPCYXFPEP-UHFFFAOYSA-N |
M.W : | 214.08 | Pubchem ID : | 612040 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H317-H319 | Packing Group: | |
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 |
---|---|---|
81% | With sodium hydride; In 1,4-dioxane; mineral oil; for 16.0h;Reflux; | To a solution of <strong>[76593-36-7]3-amino-6-chloro-4,5-dimethylpyridazine</strong> (450 mg, 2.86 mmol, 1 eq) and 2- bromo-1,3-benzothiazole (672 mg, 3.14 mmol, 1.1 eq) in 1,4-dioxane (20 mL) was added sodium hydride (60% dispersion; 457 mg, 11.42 mmol, 4 eq) portionwise and the mixture was refluxed for 16 h. The reaction mixture was allowed to cool to ambient temperature and then quenched with acetic acid. The mixture was diluted with ethyl acetate (200 mL) and washed with aqueous saturated sodium bicarbonate (100 mL), and brine (100 mL). The organic extract was dried (magnesium sulfate) and concentrated in vacuo. Purification by automated flash column chromatography (CombiFlash Rf, 40 g RediSep silica cartridge) eluting with a gradient of 0- 3% methanol in dichloromethane afforded the desired product as a yellow solid (673 mg, 2.32 mmol, 81%). LC/MS (C13H11ClN4S) 291 [M+H]+; RT 1.22 (LCMS-V-B1) 1H NMR (400 MHz, DMSO-d6) d 11.80 (br s, 1H), 7.86 (d, J = 7.75 Hz, 1H), 7.50 (s, 1H), 7.40 (td, J = 1.28, 7.69 Hz, 1H), 7.22 (t, J = 7.67 Hz, 1H), 2.37 (s, 3H), 2.33 (s, 3H). |
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