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

HRID 470114Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 470114
[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]

Komponenten

7

Edukt 3

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

Produkt 1

HCID 574702662-Tert-butyl-5-aminobenzene-1-sulfonamideAusbeute 102,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-db2765a33e2343d9a414fb5fcf5e5d37
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629162B2

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