Pyridine → N-(2-fluoro-5-nitrophenyl)methanesulfonamide

HRID 441121Notes

Reaction equation

HRID 441121 reaction equation
N1C=CC=CC=1.[F:7][C:8]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:9]=1[NH2:10].[CH3:18][S:19](Cl)(=[O:21])=[O:20]>O>[F:7][C:8]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:9]=1[NH:10][S:19]([CH3:18])(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 677852-Fluoro-5-nitroaniline

Product 1

HCID 4416401N-(2-fluoro-5-nitrophenyl)methanesulfonamideYield 72.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 334 ml of a pyridine solution containing 52.1 g of 2-fluoro-5-nitroaniline was added 42.1 g of methanesulfonyl chloride under ice-cooling, followed by stirring at room temperature for 7 hours. Water was added to the reaction solution, the precipitate was collected by filtration, and the crude crystals were recrystallized from ethanol to give 56.9 g of N-(2-fluoro-5-nitrophenyl)methanesulfonamide as pale yellow needles.

Workup

  1. temperaturecooling
  2. filtrationthe precipitate was collected by filtration
  3. customthe crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-186308195b6b45559ca1ed03d6fd5297
Source dataset
uspto-grants-1996_05
Patent number
US05521311

Reaction notes

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