Sodium Hydroxide → N-(2-fluoro-5-nitrophenyl)methanesulfonamide

HRID 379712Notes

Reaction equation

HRID 379712 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].[CH3:12][S:13](Cl)(=[O:15])=[O:14].[OH-].[Na+]>N1C=CC=CC=1>[F:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH:4][S:13]([CH3:12])(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 677852-Fluoro-5-nitroaniline

Product 1

HCID 4416401N-(2-fluoro-5-nitrophenyl)methanesulfonamideYield 92.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Fluoro-5-nitroaniline (15.7 g) solution in pyridine (100 ml) was added drop-wise with methanesulfonylchloride (17.2 g) in an ice bathing. After being stirred for 2 hours at room temperature, the reaction mixture was added with 2N sodium hydroxide (200 ml) and washed with hexane (200 ml) two times. 2N HCl (300 ml) was added into the resultant aqueous layer and solids separated were collected by filtration, washed with water and dried under vacuum to obtain 2′-fluoro-5′-nitromethanesulfonanilide (21.8 g) as brownish solid.

Workup

  1. washwashed with hexane (200 ml) two times
  2. addition2N HCl (300 ml) was added into the resultant aqueous layer and solids
  3. customseparated
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-df1134b856864423874199cf3b03823e
Source dataset
uspto-grants-2001_10
Patent number
US06300368B1

Reaction notes

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