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

HRID 470114Notes

Reaction equation

HRID 470114 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-db2765a33e2343d9a414fb5fcf5e5d37
Source dataset
uspto-grants-2014_01
Patent number
US08629162B2

Reaction notes

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