Hydrochloric Acid → N-(2,5-difluorophenyl)-4-methylbenzenesulfonamide

HRID 1030984Notes

Reaction equation

HRID 1030984 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:3]=1[NH2:4].[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.Cl>N1C=CC=CC=1>[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:4][C:3]2[CH:5]=[C:6]([F:9])[CH:7]=[CH:8][C:2]=2[F:1])(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 677752,5-Difluoroaniline

Product 1

HCID 8500594N-(2,5-difluorophenyl)-4-methylbenzenesulfonamideYield 76.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred mixture of 15.0 g (0.116 mole) of 2,5-difluoroaniline and 24.4 g (0.128 mole) of 4-methylphenylsulfonyl chloride in 50 ml of pyridine was heated at reflux for approximately 18 hours. The reaction mixture was cooled and poured into 500 ml of 6N hydrochloric acid. This acidic mixture was allowed to stand at room temperature for two days. A precipitate formed and was collected by filtration. The filter cake was washed with dilute hydrochloric acid and was dried under reduced pressure to yield 25.0 g of N-(4-methylphenylsulfonyl)-2,5-difluoroaniline. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for approximately 18 hours
  3. temperatureThe reaction mixture was cooled
  4. customA precipitate formed
  5. filtrationwas collected by filtration
  6. washThe filter cake was washed with dilute hydrochloric acid
  7. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-4b70bd8223ab439ebaa6eeca84af8c02
Source dataset
uspto-grants-1992_04
Patent number
US05108486

Reaction notes

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