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

HRID 1805061Notes

Reaction equation

HRID 1805061 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-1a7b02f48ad64fb0ae1a61086244c875
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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