Sulfur Dioxide → HCID 15029429, compound

HRID 1588453Notes

Reaction equation

HRID 1588453 reaction equation
C([Li])CCC.[CH2:6]([S:8]([N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)(=[O:10])=[O:9])[CH3:7].[S:16](=[O:18])=[O:17].C([O-])(=O)C.[Na+].[NH2:24]OS(O)(=O)=O>CCCCCC.O1CCCC1.O>[N:11]1([S:8]([CH:6]([S:16]([NH2:24])(=[O:18])=[O:17])[CH3:7])(=[O:10])=[O:9])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

9

Reactant 5

HCID 1119Sulfur DioxideHCID 76284hydroxylamine-O-sulfonic acidHCID 517045Sodium AcetateHCID 43871441-ethylsulfonylpyrrolidineHCID 178418339Butyllithium

Product 1

HCID 15029429HCID 15029429, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Under an N2 atmosphere, 68.8 ml (0.11 mol) of a 1.6N solution of n-butyllithium in hexane are added dropwise at -78° C. to 16.3 (0.1 mol) of 1-ethylsulfonylpyrrolidine in 150 ml of absolute tetrahydrofuran. After 6 hours at -78° C., 26.0 g (0.4 mol) of sulfur dioxide are passed in at the same temperature, the mixture is subsequently allowed to come to room temperature, and stirring is continued for 14 hours. Evaporation of the reaction solution gives a crude sulfinate which is dissolved in 300 ml of water without purification. 18.0 g (0.22 mol) of sodium acetate in 20 ml of water and 12.4 g (0.11 mol) of hydroxylamine-O-sulfonic acid in 10 ml of water are added in succession, and the mixture is stirred for 7 hours at room temperature. The water phase is extracted using ethyl acetate, and the organic phase is dried and evaporated. For purification, the crude product obtained in this manner is taken up in 200 ml of 2N sodium hydroxide solution, the water phase is washed 3 times using 100 ml portions of diethyl ether, and the water phase is acidified with hydrochloric acid to pH 2 and extracted using ethyl acetate. After the organic phase has been dried and evaporated, 12.8 g (53% of theory) of 1-pyrrolidinosulfonylethanesulfonamide of melting point 78°-80° C. remain.

Workup

  1. customto come to room temperature
  2. waitis continued for 14 hours
  3. customEvaporation of the reaction solution
  4. customgives a crude sulfinate which
  5. stirringthe mixture is stirred for 7 hours at room temperature
  6. extractionThe water phase is extracted
  7. customthe organic phase is dried
  8. customevaporated
  9. customFor purification

Sources & evidence

ORD record
ord-769fe3cc9ba34893b9967d0554ce63ba
Source dataset
uspto-grants-1993_06
Patent number
US05223017

Reaction notes

Loading…