Methanesulfonyl chloride → N-(2-fluoro-4-nitrobenzyl)methanesulfonamide

HRID 1428738Notes

Reaction equation

HRID 1428738 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][NH2:12].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>N1C=CC=CC=1.ClCCl>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][NH:12][S:14]([CH3:13])(=[O:16])=[O:15]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 45121148(2-Fluoro-4-nitrophenyl)methanamine

Product 1

HCID 86679366N-(2-fluoro-4-nitrobenzyl)methanesulfonamideYield 88.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2-fluoro-4-nitrophenyl)methanamine (194 mg, 1.140 mmol) in pyridine, cooled to 0° C., were added methanesulfonyl chloride (248 mg, 2.166 mmol). The resulting reaction mixture was stirred for 1 h at room temperature. The mixture was dissolved in dichloromethane and washed with 1N HCl. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. N-(2-Fluoro-4-nitrobenzyl)methanesulfonamide (250 mg) was obtained as 88% yield.

Workup

  1. customThe resulting reaction mixture
  2. washwashed with 1N HCl
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate removed in vacuo
  6. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-943dac51f85845d9b70727e7e4d5244d
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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