Reacción #1269818

ord-743a5e0d384245d08e02a78be2e9a0ac

Ecuación de reacción

O=[N+]([O-])c1c(S(=O)(=O)[O-])sc2ccccc12
mono nitro-benzothiophene-2-sulfonate
O=C([O-])[O-].[Ag+2]
silver carbonate
CCCCCC.CCOC(C)=O
hexane ethyl acetate
O=[N+]([O-])c1c(S(=O)(=O)[O-])sc2ccccc12.[Ag+]
Silver mono nitro-benzo[b]thiophene-2-sulfonate
Rendimiento 98.2%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    FiltraciónThe mixture was filtered through half an inch of Celite®
  2. 2
    Lavadothe solid was washed with 3×40mL acetonitrile
  3. 3
    Otroorganic solvent was removed via rotary evaporator to dryness and thus afforded 0.668 g of viscous solid with a yield of 98.2%
  4. 4
    OtroThe resulting compound was not purified for further reactions

Procedimiento

To a solution of mono nitro-benzothiophene-2-sulfonate (0.5177 g, 1.86 mmol) in 50 mL of acetonitrile and 1 mL of water was added silver carbonate (0.6169 g, 2.24 mmol) in portions in darkness. The resulting suspension was stirred overnight for 9 days, until no starting material is shown on the thin layer chromatography with an eluent of hexane/ethyl acetate (1:4). The mixture was filtered through half an inch of Celite® and the solid was washed with 3×40mL acetonitrile. The organic filtrate was combined and organic solvent was removed via rotary evaporator to dryness and thus afforded 0.668 g of viscous solid with a yield of 98.2%. The resulting compound was not purified for further reactions.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08663901B2uspto-grants-2014_03