Hydrochloric Acid → N-(2-Cyano-4-fluoro-phenyl)-methanesulfonamide

HRID 1015892Notes

Reaction equation

HRID 1015892 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[C:4]#[N:5].[CH3:11][S:12]([NH2:15])(=[O:14])=[O:13].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[C:4]([C:3]1[CH:6]=[C:7]([F:10])[CH:8]=[CH:9][C:2]=1[NH:15][S:12]([CH3:11])(=[O:14])=[O:13])#[N:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 72879MethanesulfonamideHCID 1235582,5-Difluorobenzonitrile

Product 1

HCID 66876859N-(2-Cyano-4-fluoro-phenyl)-methanesulfonamideYield 34.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

(Step 1) A suspension of 2,5-difluorobenzonitrile (12.4 g), methanesulfonamide (9.3 g) and potassium carbonate (13.6 g) in DMSO (360 ml) was stirred overnight at 120° C. The reaction solution was poured into 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to give N-(2-cyano-4-fluorophenyl]methanesulfonamide (6.57 g) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-7d4340dfc9404242bb30ad8729fb6707
Source dataset
uspto-grants-2011_07
Patent number
US07985863B2

Reaction notes

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