Ammonium Hydroxide → 2-Tert-butyl-5-nitrobenzene-1-sulfonamide

HRID 2404801Notes

Reaction equation

HRID 2404801 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[S:14](Cl)(=[O:16])=[O:15])([CH3:4])([CH3:3])[CH3:2].[NH4+:18].[OH-]>CCOCC.O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[S:14]([NH2:18])(=[O:16])=[O:15])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 574702642-Tert-butyl-5-nitrobenzene-1-sulfonyl chloride

Product 1

HCID 574702652-Tert-butyl-5-nitrobenzene-1-sulfonamideYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-tert-butyl-5-nitrobenzene-1-sulfonyl chloride (100 mg, 0.36 mmol) in ether (2 mL) was added aqueous NH4OH (128 μL, 3.6 mmol) at 0° C. The mixture was stirred at room temperature overnight, diluted with water and extracted with ether. The combined ether extracts were washed with brine and dried over Na2SO4. After removal of solvent, the residue was purified by column chromatography (0-50% EtOAc-Hexane) to give 2-tert-butyl-5-nitrobenzene-1-sulfonamide (31.6 mg, 34%).

Workup

  1. extractionextracted with ether
  2. washThe combined ether extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customAfter removal of solvent
  5. customthe residue was purified by column chromatography (0-50% EtOAc-Hexane)

Sources & evidence

ORD record
ord-bb10fe5956114715a5871fcf4dc0fa09
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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