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CAS No. : | 6258-06-6 | MDL No. : | MFCD00019160 |
Formula : | C14H7BrNNaO5S | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | TXMRAEGWZZVGIH-UHFFFAOYSA-M |
M.W : | 404.17 | Pubchem ID : | 5076555 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P305+P351+P338 | UN#: | |
Hazard Statements: | H319 | Packing Group: | |
GHS Pictogram: |
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* 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 |
---|---|---|
With copper; In aq. phosphate buffer; at 80 - 120℃;pH 6 - 7;Microwave irradiation; | General procedure: Sodium 1-amino-4-ar(alkyl)amino-2-sulfoanthraquinone derivatives were synthesized according to described procedures, using a Cu0-catalyzed microwave-assisted Ullmann-coupling reaction. The following general procedure was applied: A 10 mL microwave vial was charged with bromaminic acid sodium salt (7,0.2?1 mmol) and the respective amine (1.25?3 equiv). A buffer solution of Na2HPO4 (pH 9.6, 4.5 mL) and NaH2PO4 (pH 4.2,0.5 mL) and finely powdered elemental copper (0.002?0.003 g, 5-10 mol percent) were then added. The mixture was irradiated in the microwave oven at 80?120°C for 5-24 min (Scheme 1). After cooling to room temperature, ca. 200 mL of water was added to the filtrate and the aqueous solution was extracted 2?3 times with dichloromethane (200 mL). If needed the organic layer was washed with water and NaOH (0.1 N) to enhance transfer of the product to water. The aqueous layer was then concentrated in vacuo to a volume of 10?20 mL, and subsequently submitted to flash column chromatography using a gradient of acetone in water (5?60percent) as the eluent. Fractions containing blue product were collected. The solvent was evaporated by rotary evaporation to remove acetone and reduce the water volume. Complete removal of water was then achieved by lyophilization using a freeze dryer affording the product as a blue powder. For some compounds the last step of purification (RP-18 flash chromatography) had to be repeated two to three times to obtain pure product (P95percent purity as determined by HPLC-UV (254 nm)-ESI-MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With copper; In aq. phosphate buffer; at 100 - 120℃;Microwave irradiation; | General procedure: To a 30 mL microwave reaction vial, buffer solution of 0.2 M Na2HPO4 (3 mL) and 0.12 M NaH2PO4 (5 mL), bromaminic acid sodium salt (0.2 g, 0.495 mmol), a catalytic amount (~4 mg) of copper powder and the appropriate aniline or amine derivative (0.99 mmol) were added. The resulting suspension was capped and irradiated in the microwave oven for 5-20 min at 100-120 C. The reaction mixture was then cooled to room temperature, filtered and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (eluted with methanol/ethyl acetate, 1:49 (v/v)) to furnish the anilinoanthraquinone derivatives as blue solids. |
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