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CAS No. : | 39093-93-1 | MDL No. : | MFCD05861623 |
Formula : | C4H9NO2S | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | NDOVLWQBFFJETK-UHFFFAOYSA-N |
M.W : | 135.18 | Pubchem ID : | 6484228 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H332-H335 | 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 |
---|---|---|
With 1-methyl-pyrrolidin-2-one; N-ethyl-N,N-diisopropylamine; at 135℃; for 27.0h; | (1) A mixture of <strong>[79055-52-0]2,4-dibromo-6-methylpyridine</strong> (0.50 g), thiomorpholine 1,1-dioxide (0.32 g), N,N-diisopropylethylamine (0.70 mL), and N-methylpyrrolidone (2.0 mL) was stirred at 135C for 27 h. The reaction mixture was cooled to room temperature, followed by addition of water, and the mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, then the desiccant was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate = 1:1 - ethyl acetate) to obtain 4-(2-bromo-6-methylpyridin-4-yl)thiomorpholine 1,1-oxide (0.11 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In water; at 100℃; for 16h;Inert atmosphere; | [1357] 4-(1,1-dioxidothiomorpholino)benzaldehyde : To a solution of 4-fluorobenzaldehyde (0.4 g, 3.22 mmol, 1.0 eq.) and thiomorpholine 1,1-dioxide (0.65 g, 4.83 mmol, 1.5 eq.) in water (20.0 mL) was added K2CO3 (0.67 g, 4.83 mmol, 1.5 eq.). The mixture was stirred at 100C. for 16 h under N2 atmosphere. TLC (30% EtOAc in hexane) showed the reaction was completed. The reaction was cooled to room temperature and was extracted with EtOAc (2100 mL). The organic layer was dried over anhydrous Na2SO4, concentrated under reduced pressure to get the crude. The crude product was purified by flash column chromatography using 25-30% EtOAc in hexane as an eluent to give 4-(1,1-dioxidothiomorpholino)benzaldehyde. LC-MS (m/z)=240.1[M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.12 (s, 4H), 3.95 (s, 4H), 7.14 (d, J=8.8 Hz, 2H), 7.74 (d, J=8.8 Hz, 2H), 9.74 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.56% | With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃;Inert atmosphere; Sealed tube; | Methyl 4-bromo-2,6-dichloro-benzoate (70 mg, 246.54 umol), 1,4-thiazinanel,1-dioxide hydrochloride (50.78 mg, 295.84 umol), diacetoxypalladium (2.77 mg, 12.33 umol), binap (9.21 mg, 14.79 umol), Cesium carbonate (240.98 mg, 739.61 umol) in toluene (5 mL) was added to a nitrogen-filled sealed tube, and the subsequent reaction mixture was stirred at 100 C. overnight, TLC showed that the starting material was consumed, then the reaction mixture was diluted with DCM, and filtered to collect the filtrate. The crude material was purified by silica gel column (PE:EA=4:1) to afford methyl 2,6-dichloro-4-(1,1-dioxo-1,4-thiazinan-4-yl)benzoate (63 mg, 186.28 umol, 75.56% yield) LC-MS (Agilent LCMS 1260-6120, Column: Waters X-Bridge C18 (50 mm*4.6 mm*3.5 μm); Column Temperature: 40 C.; Flow Rate: 1.5 mL/min; Mobile Phase: from 95% [water+10 MmNH4HCO3] and 5% [CH3CN] to 5% [water+10 MmNH4HCO3] and 95% [CH3CN] in 2 min, then under this condition for 2 min. Purity is 100%. Rt=2.362 min; MS Calcd.: 337.0; MS Found: 337.8 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 6.80 (s, 2H), 3.95 (s, 3H), 3.92-3.85 (m, 4H), 3.13-3.05 (m, 4H). |
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