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CAS No. : | 51498-37-4 | MDL No. : | MFCD02093473 |
Formula : | C5H5NO4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AZRCSTMIVMQIPR-UHFFFAOYSA-N |
M.W : | 175.16 | Pubchem ID : | 3016673 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 | UN#: | N/A |
Hazard Statements: | H315-H319 | Packing Group: | N/A |
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 |
---|---|---|
95% | With phosphorus pentachloride; trichlorophosphate; at 125℃; for 1.0h; | 4-chloropyridine-3-sulfonyl chloridePentachlorophosphorane (7.29 g, 35 mmol), phosphoryl trichloride (1.86 ml_, 20 mmol) were added to <strong>[51498-37-4]4-hydroxypyridine-3-sulfonic acid</strong> (1.75 g, 10 mmol). The mixture was stirred at 125 C for 1 h. The solution was allowed to cool to 23 C and then concentrated to remove excess POCI3, diluted with Et20 and poured onto ice. The residue was stirred for 5 min and then was neutralized with solid NaHC03, the mixture was extracted with EtOAc and combined extracts were dried (Na2S04) and concentrated giving 2.02 g (95%) of the title compound. LC-MS m/z 211.8 (M+H)+, 0.74 (ret. time). |
84% | With phosphorus pentachloride; at 0 - 120℃; for 1.0h; | To a suspension of <strong>[51498-37-4]4-hydroxypyridine-3-sulfonic acid</strong> (17 .5 g, 1 00 mmol) at 0 oc wasadded PCis (72.8 g, 350 mmol) and POCb (18.62 ml, 200 mmol). It was heated at 120 oc10 for 1 h. The reaction mixture was cooled to ambient temperature and concentrated. It wasdiluted with EtOAc and poured over ice. Solid NaHC03 was added and extracted withEtOAc. The organic layer was dried over anhydrous Na2S04 and filtered. The filtrate wasconcentrated to give the title compound (18 g, 84 mmol, 84 % yield) as pale yellow liquid.LC/MS m/z = 211.96 (M+Ht, 1.94 min (ret. time). |
68.6% | With phosphorus pentachloride; trichlorophosphate; at 0 - 120℃; for 1.0h; | To a suspension of <strong>[51498-37-4]4-hydroxypyridine-3-sulfonic acid</strong> (25 g, 143 mmol) was added PCI5 (104 g, 500 mmol) and POCI3 (26.6 ml, 285 mmol) at 0 C and stirred at 120 C for 1 h. The reaction mixture was cool to ambient temperature, the reaction mass was concentrated. The residue was diluted with EtOAc and poured in to ice. Solid NaHC03 was added and the aqueous phase was extracted with EtOAc. The organic layer was dried over anhydrous Na2S04 and filtered to afford the title compound (25 g, 98 mmol, 68.6% yield). LCMS mfz 212 (M+H)+, 1.93 min (ret. time). |
68.6% | With phosphorus pentachloride; trichlorophosphate; at 0 - 120℃; for 1.0h; | To a suspention of <strong>[51498-37-4]4-hydroxypyridine-3-sulfonic acid</strong> (25 g, 143 mmol) was added PCl5 (104 g, 500 mmol) and POCl3 (26.6 ml, 285 mmol) at 0 C and stirred at 120 C for 1h. The reaction mixture was cool to ambient temperature, the reaction mass was concentrated. The residue was diluted with EtOAc and poured in to ice. Solid NaHCO3 was added and the aqueous phase was extractred with EtOAc.The organic layer was dried over anhydrous Na2SO4 and filtered to afford the title compound (25 g, 98 mmol, 68.6% yield). LCMS m/z 212 (M+H)+, 1.93 min (ret. time). |
With phosphorus pentachloride; trichlorophosphate; | (1) 80 g of phosphorus pentachloride, 80 g of phosphorus oxychloride and 20 g of <strong>[51498-37-4]4-hydroxy-3-pyridinesulfonic acid</strong> were mixed and reacted under reflux for 4.5 hours to obtain a reaction mixture containing 4-chloro-3-chlorosulfonylpyridine. From the obtained reaction mixture, excess phosphorus oxychloride was distilled off under reduced pressure. The residue was put into ice of about 200 g and extracted with dichloromethane. The obtained extract layer was washed with a saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate and cooled with ice. | |
With phosphorus pentachloride; In chlorobenzene; for 6.0h;Heating / reflux; | Example 2; 4-Chloro-3-pyridinesulfonamide [4]. "One-pot"procedure:; A mixture of <strong>[51498-37-4]4-hydroxy-3-pyridinesulfonic acid</strong> [5] (50.0 g, 0.29 mol), phosphorus pentachloride (130. 8 g, 0.63 mol) and chlorobenzene (580 g) was stirred under reflux conditions for 6 hours. The mixture of phosphorus oxychloride and chlorobenzene (590-610 g) were distilled off from the mixture at atmospheric pressure. The cooled (25-30 C) residue (-100 mL) was added dropwise to the stirred mixture of 25 % aqueous ammonia (116.5 g, 1.7 mol) and acetone (20 g) for 30-40 minutes maintaining the temperature at 0-5 C. The reaction mixture (pH 11-12) was stirred for 1 hour at the same temperature and for 1 hour at 25 C. Chlorobenzene (50 g) and water (150 g) were added to the stirred mixture at the same temperature. The reaction mixture was concentrated to 250-300 g (pH 7-8) under reduced pressure (20 - 100 mbar) at 30-40 C. The obtained suspension was stirred for 5 hours at 0- 5 C. The precipitated solids were filtered off, triturated with water (2 x 200 g) at 30 C and dried under reduced pressure at 40-50 C (water bath) to a constant weight to give 42.7 g (77.6 %) of 4-chloro-3-pyridinesulfonamide [4] with 99.6 % purity by HPLC, assay 99.9 % by HC104 titration, 0.06 % of water by KF titration and mp 146-148 C (dec. ). | |
With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In 1,2-dichloro-ethane; at 90℃; for 0.75h; | 4-Chloro-N-(3,4-dimethoxyphenyl)pyridine-3-sulfonamide (IntDI ) A solution of <strong>[51498-37-4]4-hydroxypyridine-3-sulfonic acid</strong> (5.0 g, 28.5 mmol), N,N- di/'sopropylethylamine (9.2 g, 71.3 mmol), phosphorus(V) oxychloride (10.9 g, 71.3 mmol) in 1 ,2-dichloroethane (50 mL) was heated at 90C for 45 min with TLC monitoring (hexane:EtOAc, 1 :1). After cooling, the solution was added to 3,4- dimethoxyaniline (4.8 g, 31.0 mmol), A/./V-di/sopropylethylamine (7.35 g, 57.0 mmol) in 1 ,2-dichloroethane (50 mL) at -10C and the resulting mixture stirred for approximately 2 h at rt with TLC monitoring (hexane:EtOAc, 1 :1). The mixture was then added to saturated aqueous NaHC03 (200 mL), extracted with DCM (3 x 50 mL) and the combined organic layers dried over Na2S04 and concentrated in vacuo. Purification by gradient column chromatography eluting with 0-20% EtOAc in hexane yielded the title compound (2.2 g, 6.69 mmol). Mass spectroscopy: (ESI +ve) 329.2, 331.2 [M+H]+1H NMR: (400 MHz, DMSO) delta 3.65 (s, 3H), 3.65 (s, 3H), 6.60 (dd, J=8.5, 2.4, 1 H), 6.72 (d, J=2.4, 1 H), 6.81 (d, J=8.9, 1 H), 7.78 (d, J=5.2, 1 H), 8.72 (d, J=5.2, 1 H), 8.96 (s, 1 H), 10.52 (br s, 1 H) |