Methanesulfonyl chloride → 3'-Acetyl-4'-fluoromethanesulfonanilide

HRID 2379182Notes

Reaction equation

HRID 2379182 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14]>C(OCC)(=O)C.N1C=CC=CC=1>[C:8]([C:6]1[CH:7]=[C:2]([CH:3]=[CH:4][C:5]=1[F:11])[NH:1][S:13]([CH3:12])(=[O:15])=[O:14])(=[O:10])[CH3:9]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 27811251-(5-Amino-2-fluorophenyl)ethanone

Product 1

HCID 111071753'-Acetyl-4'-fluoromethanesulfonanilideYield 79.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

5'-Amino-2'-fluoroacetophenone (28 g) was dissolved in a mixture of 100 ml of ethyl acetate and 15.9 g of pyridine, a solution of 23 g of methanesulfonyl chloride in 50 ml of ethyl acetate was added with ice-cooling and stirring and the mixture was made to react at room temperature for 3 hours. The reaction mixture was washed with water, dried, the solvent was evaporated therefrom and the residue was purified by silica gel column chromatography (eluting with chloroform) to give 33.7 g of 3'-acetyl-4'-fluoromethanesulfonanilide, m.p. 120°-123° C.

Workup

  1. temperaturecooling
  2. customto react at room temperature for 3 hours
  3. washThe reaction mixture was washed with water
  4. customdried
  5. customthe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (eluting with chloroform)

Sources & evidence

ORD record
ord-dd1fe4f51b8b424aa42709379c69d79f
Source dataset
uspto-grants-1994_11
Patent number
US05360822

Reaction notes

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