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

HRID 2258616Notes

Reaction equation

HRID 2258616 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 100.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred solution of 10.0 grams (0.077 mole) of 2,5-difluoroaniline and 16.2 grams (0.085 mole) of 4-methylphenylsulfonyl chloride in 50 mL of pyridine was heated at reflux for about 2.5 hours. The reaction mixture was then cooled and poured into ice-cold aqueous 3N hydrochloric acid. The resultant solid was collected by filtration and dried, yielding 22.0 grams of N-(4-methylphenylsulfonyl)-2,5-difluoroaniline. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureat reflux for about 2.5 hours
  2. temperatureThe reaction mixture was then cooled
  3. filtrationThe resultant solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-f11e8eb439c64907b1386bc5d0f705dd
Source dataset
uspto-grants-1997_08
Patent number
US05661108

Reaction notes

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