ChemicalBook CAS DataBase List pyridine-3-sulfonyl chloride

pyridine-3-sulfonyl chloride synthesis

8synthesis methods

Product Name:pyridine-3-sulfonyl chloride
CAS Number:16133-25-8
Molecular formula:C5H4ClNO2S
Molecular Weight:177.61

Add thionyl chloride to the water, cool to about 0-5°C, and add cuprous chloride. Fluoboric acid diazonium salt was added to the solution and reacted at 0-5°C overnight. The reaction solution was extracted with dichloromethane, combining the organic layers. The organic layer was washed once with saturated aqueous sodium bicarbonate solution, once with water, and finally once with saturated brine. The product was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated to remove methylene chloride to obtain the product pyridine-3-sulfonyl chloride with a yield of 90.7%.

636-73-7 Synthesis

636-73-7
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16133-25-8
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Yield:16133-25-8 94%

Reaction Conditions:

with phosphorus pentachloride;trichlorophosphate for 3 h;Heating / reflux;

Steps:

B.1.1

A mixture of pyridine-3-sulfonic acid (10.3 g, 64.8 mmol), phosphorus pentachloride (20.82 g, 100 mmol) and phosphorus oxychloride (10 mL, 109 mmol) was heated to reflux for 3 h (according to J. Org. Chem. 1989, 54(2), 389.). Evaporated to dryness to give a yellow solid, dissolved in ice water and methyl-tert-butyl ether, added cautiously sat. NaHCO₃-sol. until neutralized, saturated with solid NaCl, separated phases, dried organic layer over Na₂SO₄. Removal of the solvent in vacuum to give the title compound as an orange liquid (10.85 g, 94%). MS (ISP) 178.1 [(M+H)⁺] and 180.0 [(M+2+H)⁺].

References:

US2006/217387,2006,A1 Location in patent:Page/Page column 25

462-08-8 Synthesis