Hydrochloric Acid → Methanesulfonamide, N-[4-acetyl-2-[(2,4-difluorophenyl)thio]phenyl]-

HRID 1087204Notes

Reaction equation

HRID 1087204 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[S:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19].[CH3:20][S:21](Cl)(=[O:23])=[O:22].Cl>N1C=CC=CC=1>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:21]([CH3:20])(=[O:23])=[O:22])=[C:3]([S:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])[CH:4]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 10062143HCID 10062143, compound

Product 1

HCID 10450972Methanesulfonamide, N-[4-acetyl-2-[(2,4-difluorophenyl)thio]phenyl]-Yield 50.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4'-amino-3'-(2,4-difluorophenylthio)acetophenone (2.0 g) and methanesulfonyl chloride (1.0 g) in pyridine (20 ml) was stirred overnight at room temperature. The mixture was poured into cold diluted hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried, and concentrated under reduced pressure. The residue was recrystallized from ethanol to give yellow crystals of 4'-acetyl-2'-(2,4-difluorophenylthio)methanesulfonanilide (1.3 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-c57670d4ca4945e49f31d86191f8eb9c
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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