Sodium Cyanide → HCID 59206579, compound

HRID 83754Notes

Reaction equation

HRID 83754 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 59206579HCID 59206579, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-82a1e2f7e0d24c0290860ed994109833
Source dataset
uspto-grants-2014_09
Patent number
US08846753B2

Reaction notes

Loading…