Stannous chloride dihydrate → 2-Tert-butyl-5-aminobenzene-1-sulfonamide

HRID 2404802Notes

Reaction equation

HRID 2404802 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[S:14]([NH2:17])(=[O:16])=[O:15])([CH3:4])([CH3:3])[CH3:2].O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CCO.CCOC(C)=O.O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[S:14]([NH2:17])(=[O:15])=[O:16])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 574702652-Tert-butyl-5-nitrobenzene-1-sulfonamide

Product 1

HCID 574702662-Tert-butyl-5-aminobenzene-1-sulfonamideYield 102.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-tert-butyl-5-nitrobenzene-1-sulfonamide (32 mg, 0.12 mmol) and SnCl2.2H2O (138 mg, 0.61 mmol) in EtOH (1.5 mL) was heated in microwave oven at 100° C. for 30 min. The mixture was diluted with EtOAc and water, basified with sat. NaHCO3 and filtered through Celite. The organic layer was separated from water and dried over Na2SO4. Solvent was removed by evaporation to provide 2-tert-butyl-5-aminobenzene-1-sulfonamide (E-7) (28 mg, 100%), which was used without further purification. HPLC ret. time 1.99 min, 10-99% CH3CN, 5 min run; ESI-MS 229.3 m/z (MH+).

Workup

  1. filtrationfiltered through Celite
  2. customThe organic layer was separated from water
  3. dry with materialdried over Na2SO4
  4. customSolvent was removed by evaporation

Sources & evidence

ORD record
ord-8ca7df0fc6114d1bafa5532f6667c3c7
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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