Hydrochloric Acid → N-Hydroxy-N,4-dimethylbenzene-1-sulfonamide

HRID 653997Notes

Reaction equation

HRID 653997 reaction equation
[CH3:1][NH:2][OH:3].Cl.[C:5]1([CH3:15])[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1.[Cl-].[Na+]>C(N(CC)CC)C.O1CCCC1>[CH3:1][N:2]([S:11]([C:8]1[CH:9]=[CH:10][C:5]([CH3:15])=[CH:6][CH:7]=1)(=[O:13])=[O:12])[OH:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 73974-Toluenesulfonyl chlorideHCID 11647Methylhydroxylamine

Product 1

HCID 21698657N-Hydroxy-N,4-dimethylbenzene-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

5.02 Grams of N-methylhydroxylamine.HCl was suspended with 70 ml of tetrahydrofuran and 6.70 g of triethylamine was added to the solution. After stirring at room temperature for 0.5 hour, 5.73 g of p-toluenesulfonyl chloride was added to the reaction solution and stirred at room temperature over night. The saturated sodium chloride solution was added to the reaction solution and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and N-methyl-N-(p-toluenesulfonyl)hydroxylamine was obtained.

Workup

  1. additionwas added to the solution
  2. stirringstirred at room temperature over night
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0510776116ae43ada788a5b58af05641
Source dataset
uspto-grants-1992_07
Patent number
US05129938

Reaction notes

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