Reaction #4820

Reaction equation

hydrogen chloride

sodium 1-(methylsulfonyl)ethanesulfonate

Formula II

sodium 1-(methylsulfonyl)ethanesulfonate

phosphorus pentachloride

→

1-(Methylsulfonyl)ethanesulfonyl Chloride

Solvents

dichloromethane

Conditions

Workup

1. 1
   TemperatureThe mixture was maintained at 80°-100° C. overnight
2. 2
   Temperaturecooled
3. 3
   FiltrationThe mixture was filtered
4. 4
   Washthe residue was washed with dichloromethane
5. 5
   Otherthe solvent was evaporated from the dichloromethane solution (combined portions) with a stream of nitrogen
6. 6
   ConcentrationThe residual oil was concentrated further with a vacuum pump
7. 7
   OtherMS (electron-impact, direct-probe temperature 20° C.), m/e 207 (M+1), 171 (M - Cl)

Procedure

A mixture of 5 g of sodium 1-(methylsulfonyl)ethanesulfonate (Formula II, X=R=CH3, Y=Na) and 5.34 g of phosphorus pentachloride was stirred under an inert atmosphere at room temperature. After about 20 minutes, the evolution of hydrogen chloride and the generation of heat were observed, and shortly thereafter the mixture became liquid. The mixture was maintained at 80°-100° C. overnight, cooled, and diluted with dichloromethane. The mixture was filtered, the residue was washed with dichloromethane, and the solvent was evaporated from the dichloromethane solution (combined portions) with a stream of nitrogen. The residual oil was concentrated further with a vacuum pump: weight of oil, 3.8 g. The mass spectrum and the proton NMR showed that this material was principally 1-(methylsulfonyl)ethanesulfonyl chloride (Formula III, R=X=CH3 and Z=Cl): MS (electron-impact, direct-probe temperature 20° C.), m/e 207 (M+1), 171 (M - Cl); 1H NMR (300.6 MHz, CDCl3), δ 2.07 (d, CH3CH), 3.32 (s, CH3SO2), 4.84 (q, CHCH3). The infrared spectrum (KBr) included strong bands at 1375, 1325, 1170, 1150, 960, 760, 715, 595, 535, 505, 490 cm-1.

Source