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CAS No. : | 376347-09-0 | MDL No. : | MFCD12776133 |
Formula : | C8H11NO3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VPZIJOVNCXBFON-UHFFFAOYSA-N |
M.W : | 201.24 | Pubchem ID : | 60661236 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 | UN#: | |
Hazard Statements: | H315-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 |
---|---|---|
90% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 1.0h; | Compound 3 To a 300 ml solution of 28.85 g (0.0945 mol) of compound 2 in THF is carefully added 5.32 g (0.140 mmol) of lithium aluminium hydride and the mixture is stirred for about 1 hr at room temperature. To the reaction mixture was added ethyl acetate and water under ice-cooling to decompose the excess of reducing agents. It was then partitioned between ethyl acetate and 2N HCI. the organic layer is washed with water and a saline, dried over MGS04, filtered and concentrated under reduced pressure to obtain a crude product. Recrystallization from methylene chloride/ether gives 22.34 g (0.0848 mol ; yield, 90%) of compound 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With pyridinium chlorochromate; In dichloromethane; at 20℃; for 1.0h; | C. 3-[(MethyIsulfonyl)amino]benzaldehyde.; [3-(Hydroxymethyl) phenyl](methylsulfonyl) amine (0.42 g, 2.08 mmol) was dissolved in dichloromethane (20 mL) followed by addition of pyridinium chlorochromate (0.67 g, 3.12 mmol). The reaction was stirred at rt for IH. Filtered crude reaction through a plug of silica gel and washed with 60% EtOAc/Hex (250 mL), removed volatiles under reduced pressure to afford the title compound (0.40 g, 2.01 mmol, 97%) as a white solid. MS (ESI) m/z 200.2 [M+l]+ [00391] |
94% | With pyridinium chlorochromate; In dichloromethane; at 20℃; for 1.16667h;Molecular sieve; | To a 1500 ml solution of 22.06 g (83.8 MMOL) of compound 3 in methylene chloride are added 44 g of molecular sieve 4A (powder) and 32.5 g (151 MMOL) of pyridinium chlorochromate and the mixture is stirred fro 70 min at room temperature. The reaction mixture is purified by column chromatography on silica gel eluting with methylene chloride to yield 20.46 g (78.3 mmol ; yield, 94% of compound 4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14.3% | With sodium hydride; In 1-methyl-pyrrolidin-2-one; toluene; at 20 - 50℃; for 16.0h; | Solid sodium hydride (18 mg, 0.75 mmol) was added to a stirred solution of the product of step (d) (28.5 mg, 0.069 mmol) and N-[3-(HYDROXYMETHYL) phenyl] -methanesulfonamide (WO 01/90070) (35 mg, 0.17 mmol) in a mixture of toluene (0.2 mL) and l-methyl-2- pyrrolidinone (0.2 mL) at RT. The reaction mixture was stirred for 16 h at 50 C. After cooling to RT, the reaction mixture was quenched with water (0.1 mL) and concentrated. The residue was dissolved in DMSO (1 mL), and purified by preparative HPLC to give 4.5 mg (14.3%) of the title compound as an off-white solid. MS (ESI+) m/z 454 [M+H] +. |
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