Hydrochloric Acid → 4-Amino-N-(1,1-dimethylethyl)benzenesulfonamide

HRID 446155Notes

Reaction equation

HRID 446155 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=O)C.[OH-].[K+].Cl>O.CO>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])=[O:12])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 668309N-[4-(tert-butylsulfamoyl)phenyl]acetamide

Product 1

HCID 8326274-Amino-N-(1,1-dimethylethyl)benzenesulfonamideYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent3×

Procedure

A solution of 4-acetylamino-N-tert-butylbenzenesulfonamide (8.0 g, 29.6 mmol), KOH (8.30 g, 148 mmol), H2O (6 mL) and MeOH (24 mL) is heated at 100° C. for 2 h. H2O (24 mL) is added and the mixture is heated for two more hours. It is allowed to cool, H2O is added and it is brought to pH 8 with 1N HCl. It is then extracted with EtOAc, dried over Na2SO4 and the solvent is removed, to give 6.0 g of the product as a white solid (yield: 89%).

Workup

  1. temperaturethe mixture is heated for two more hours
  2. temperatureto cool
  3. extractionIt is then extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. customthe solvent is removed

Sources & evidence

ORD record
ord-7accfb88a5a149a0a2568fbd23b95b7d
Source dataset
uspto-grants-2013_07
Patent number
US08476456B2

Reaction notes

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