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

HRID 1428712Notes

Reaction equation

HRID 1428712 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 over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. N-(4-bromobenzyl)methane-sulfonamide (675 mg) was obtained in 95% yield.

Workup

  1. washThe mixture was washed with water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate removed in vacuo
  5. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-be99fc43f0034857942c2e7984969292
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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