Sodium Cyanide → 4-bromo-2-cyano-N,N-dimethylbenzenesulfonamide

HRID 39188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 39188
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[C:4](F)[CH:3]=1.[C-:15]#[N:16].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[C:4]([C:15]#[N:16])[CH:3]=1

Komponenten

4

Edukt 2

HCID 8929Sodium CyanideHCID 592067474-bromo-2-fluoro-N,N-dimethylbenzenesulfonamide

Produkt 1

HCID 592065794-bromo-2-cyano-N,N-dimethylbenzenesulfonamideAusbeute 7,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Bromo-2-fluoro-N,N-dimethylbenzenesulfonamide (1.0 g, 3.5 mmol) and sodium cyanide (350 mg, 7.1 mmol) were dissolved in DMF (3 mL) and irradiated in the microwave at 150° C. for 20 minutes. DMF was removed in vacuo and the residue was redissolved in dichloromethane (5 mL). The organics were washed with 5 mL of each 1N aqueous HCl, saturated aqueous NaHCO3, and brine. Organics were dried over Na2SO4 and evaporated to dryness. Crude product was purified by chromatography on silica gel (eluting with 0-50% ethyl acetate in hexanes) to afford 4-bromo-2-cyano-N,N-dimethylbenzenesulfonamide (72 mg, 7%). ESI-MS m/z calc. 288.0, found 288.9 (M+1)+; retention time 1.44 minutes.

Aufarbeitung

  1. customirradiated in the microwave at 150° C. for 20 minutes
  2. customDMF was removed in vacuo
  3. dissolutionthe residue was redissolved in dichloromethane (5 mL)
  4. washThe organics were washed with 5 mL of each 1N aqueous HCl, saturated aqueous NaHCO3, and brine
  5. dry with materialOrganics were dried over Na2SO4
  6. customevaporated to dryness
  7. customCrude product was purified by chromatography on silica gel (eluting with 0-50% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a7aef5beb5604791b3f84f0059ae01b0
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524767B2

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