Methanesulfonyl chloride → N-[(4-bromophenyl)methyl]methanesulfonamide

HRID 1842982Notes

Reaction equation

HRID 1842982 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][CH:3]=1.[CH3:10][S:11](Cl)(=[O:13])=[O:12]>N1C=CC=CC=1.ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][S:11]([CH3:10])(=[O:13])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 775714-Bromobenzylamine

Product 1

HCID 19027423N-[(4-bromophenyl)methyl]methanesulfonamideYield 95.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-bromophenyl)methanamine (500 mg, 2.687 mmol) in pyridine were added methanesulfonyl chloride (0.4 mL, 5.106 mmol) at 0° C. The reaction mixture was stirred for 1 h, then diluted with dichloromethane. The mixture was washed with water. The organic layer was dried (MgSO4) and filtered. The solvent removed in vacuo. The crude product was purified by CC. N-(4-bromobenzyl)methanesulfonamide (675 mg) was obtained (95% yield).

Workup

  1. washThe mixture was washed with water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customThe solvent removed in vacuo
  5. customThe crude product was purified by CC

Sources & evidence

ORD record
ord-35ab45cc85a9468f8169969d6b950cf5
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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