Chloroform → 3-Tosyloxy-2,2-dimethyl-1-propanesulfonamide

HRID 1590057Notes

Reaction equation

HRID 1590057 reaction equation
[OH:1][CH2:2][C:3]([CH3:10])([CH3:9])[CH2:4][S:5]([NH2:8])(=[O:7])=[O:6].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.C(Cl)(Cl)Cl>N1C=CC=CC=1>[S:17]([O:1][CH2:2][C:3]([CH3:10])([CH3:9])[CH2:4][S:5]([NH2:8])(=[O:7])=[O:6])([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 73974-Toluenesulfonyl chlorideHCID 103296873-Hydroxy-2,2-dimethylpropane-1-sulfonamide

Product 1

HCID 100646893-Tosyloxy-2,2-dimethyl-1-propanesulfonamideYield 88.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5.0 g of 3-hydroxy-2,2-dimethyl-1-propanesulfonamide in 18 ml of pyridine was added 6.3 g of p-toluenesulfonyl chloride under ice-cooling and stirring. After 2 hours, the reaction mixture was poured into a mixture of 300 ml of chloroform and 100 ml of ice-water. The separated chloroform layer was washed in turn with diluted hydrochloric acid and water, dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain 8.5 g of 3-tosyloxy-2,2-dimethyl-1-propanesulfonamide.

Workup

  1. temperaturecooling
  2. washThe separated chloroform layer was washed in turn with diluted hydrochloric acid and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-66c8ad8b776a49c2b623497482845fa6
Source dataset
uspto-grants-1993_04
Patent number
US05202324

Reaction notes

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