Pyridine → N-(4-fluoro-3-nitrophenyl)ethanesulfonamide

HRID 1987223

Reaction equation

HRID 1987223 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[F:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16].N1C=CC=CC=1>CCOC(C)=O>[F:7][C:8]1[CH:14]=[CH:13][C:11]([NH:12][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 677684-Fluoro-3-nitroaniline

Product 1

HCID 3286362N-(4-fluoro-3-nitrophenyl)ethanesulfonamideYield 98.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

EtSO2Cl (21.5 mL, 0.22 mol) was added drop wise to a mixture of 4-fluoro-3-nitroaniline (29.6 g, 0.19 mol) and pyridine (100 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with EtOAc (1 L). The resulting solution was washed with HCl 2N (4×200 mL), NaHCO3 saturated solution (4×200 mL) and water (4×200 mL). The organic phase was dried over anhydrous Na2SO4 and the solvent was removed to provide the title product as beige solid (46.3 g)

Workup

  1. washThe resulting solution was washed with HCl 2N (4×200 mL), NaHCO3 saturated solution (4×200 mL) and water (4×200 mL)
  2. dry with materialThe organic phase was dried over anhydrous Na2SO4
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-8f16dd7439374421867574e32deead18
Source dataset
uspto-grants-2009_06
Patent number
US07550495B2

Linked notes

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