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

HRID 465932Notes

Reaction equation

HRID 465932 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 to 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 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

Sources & evidence

ORD record
ord-030acfa456e547dba0d8b30fd4fbf7c6
Source dataset
uspto-grants-1992_10
Patent number
US05155108

Reaction notes

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