Sodium Cyanide → HCID 59206579, compound

HRID 2242736Notes

Reaction equation

HRID 2242736 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-551eb555b9bb4f6fae31fde22270f509
Source dataset
uspto-grants-2010_03
Patent number
US07671221B2

Reaction notes

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