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

HRID 1492732Notes

Reaction equation

HRID 1492732 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 75.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1300 ml of a pyridine solution containing 204.0 g of 2-fluoro-5-nitroaniline was added 165.0 g of methanesulfonyl chloride under ice cooling, followed by stirring at room temperature for 24 hours. To the reaction solution was added 3000 ml of water, and the precipitate was collected by filtration, air-dried overnight and recrystallized from ethanol to give 230.0 g of N-(2-fluoro-5-nitrophenyl)methanesulfonamide as colorless needles.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. customair-dried overnight
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6fe0c93e16794f3a96c4bdc8230d2fd8
Source dataset
uspto-grants-1994_12
Patent number
US05374764

Reaction notes

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