Hydrochloric Acid → Methanesulfonylmethanesulfonyl chloride

HRID 64957

Reaction equation

HRID 64957 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:7][S:8]([CH2:11][S:12]([O-:15])(=O)=[O:13])(=[O:10])=[O:9].[Na+].Cl.CS([Cl:21])=O>P(Cl)(Cl)(Cl)=O>[CH3:7][S:8]([CH2:11][S:12]([Cl:21])(=[O:15])=[O:13])(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24819Phosphorus pentachlorideHCID 548463Methanesulfinyl chlorideHCID 23721596Sodium (methylsulfonyl)methanesulfonate2×

Product 1

HCID 556269Methanesulfonylmethanesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
70 °C

Procedure

Phosphorus pentachloride (79.3 g, 0.381 mole) and sodium (methylsulfonyl)methanesulfonate (Formula II with Y=Na, X=H and R=CH3 ; 70 g, 0.359 mole) were stirred with 150 ml of phosphorus oxychloride. As the mixture was warmed to 70° C. in an oil bath, hydrogen chloride was slowly evolved, and the slurry thinned enough to be stirred with a magnetic stirrer. The mixture was heated for 18 hours in an oil bath at 80°-90° C., cooled, and filtered, and the residue was washed with dry chloroform. The chloroform caused the product to precipitate in the filtrate. The precipitate was collected, washed with a small amount of chloroform, and dried over sodium hydroxide pellets: yield, 28.5 g (41%); mp 109°-111° C.; MS (direct-probe temperature, 20° C.) m/e 193 (M+H), 192 (M), 177 (M-CH3), 157 (CH3SO2CH2SO2), 143, 141, 113 (CH2SO2Cl), 98 (CH3SOCl), 94, 93 (CH3SO2CH2), 79 (CH3SO2), 78, 64, 63 (CH3SO); IR (cm-1, strong and medium bands) 3045, 3025, 2995 s, 2930 s, 1405, 1390 s, 1380 s, 1360, 1335 s, 1325 sh, 1315 s, 1225, 1175 s, 1160 s, 1110 s, 980 s, 965, 860 s, 760 s, 695, 595 s, 515 s, 495 s, 460 s.

Workup

  1. temperatureThe mixture was heated for 18 hours in an oil bath at 80°-90° C.
  2. temperaturecooled
  3. filtrationfiltered
  4. washthe residue was washed with dry chloroform
  5. customto precipitate in the filtrate
  6. customThe precipitate was collected
  7. washwashed with a small amount of chloroform
  8. dry with materialdried over sodium hydroxide pellets
  9. customyield
  10. customIR (cm-1, strong and medium bands) 3045, 3025, 2995 s, 2930 s, 1405, 1390 s, 1380 s, 1360, 1335 s, 1325 sh, 1315 s, 1225, 1175 s, 1160 s, 1110 s, 980 s, 965, 860 s, 760 s, 695, 595 s, 515 s, 495 s, 460 s

Sources & evidence

ORD record
ord-78af65a9e00046378c37a31f1d69b2af
Source dataset
uspto-grants-1986_09
Patent number
US04611074

Linked notes

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