Methanesulfonyl chloride → N-(3-bromo-5-cyanophenyl)methanesulfonamide

HRID 2070955Notes

Reaction equation

HRID 2070955 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:10])[CH:9]=1)[C:5]#[N:6].[CH3:11][S:12](Cl)(=[O:14])=[O:13]>C(Cl)Cl.N1C=CC=CC=1>[Br:10][C:8]1[CH:9]=[C:2]([NH:1][S:12]([CH3:11])(=[O:14])=[O:13])[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 534069613-Amino-5-bromobenzonitrile

Product 1

HCID 68670101N-(3-bromo-5-cyanophenyl)methanesulfonamideYield 88%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 502 mg of 3-amino-5-bromobenzonitrile in 6 mL of CH2Cl2 and 2 mL of pyridine at 0° C. was added 0.2 mL (2.57 mmol) of MsCl at 0° C. The ice bath was removed and stirring was continued at r.t. for 6.5 h. The solution was concentrated and EtOAc and 20 mL of H2O were added. The organic layer was washed with 15 mL of brine and water, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (35% EtOAc/hexanes) provided 617 mg of N-(3-bromo-5-cyanophenyl)methanesulfonamide as a colorless solid in 88% yield.

Workup

  1. customThe ice bath was removed
  2. concentrationThe solution was concentrated
  3. additionEtOAc and 20 mL of H2O were added
  4. washThe organic layer was washed with 15 mL of brine and water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash silica gel chromatography (35% EtOAc/hexanes)

Sources & evidence

ORD record
ord-425cd905b3054070853c4737dc9d49da
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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