Pyridine → HCID 9975363, compound

HRID 1087208Notes

Reaction equation

HRID 1087208 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH2:20])=[C:8]([CH:19]=1)[C:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18])=[O:10])(=[O:3])[CH3:2].[CH3:21][S:22](Cl)(=[O:24])=[O:23].N1C=CC=CC=1>C1C=CC=CC=1>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:20][S:22]([CH3:21])(=[O:24])=[O:23])=[C:8]([C:9](=[O:10])[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])[CH:19]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 10333588HCID 10333588, compound

Product 1

HCID 9975363HCID 9975363, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5-acetyl-2-amino-2',4'-difluorobenzophenone (3.3 g), methanesulfonyl chloride (5.5 ml) and pyridine (1 ml) in benzene (30 ml) was refluxed for 4 hours. The reaction mixture was poured into ice-water (100 ml ) and extracted with ethyl acetate (100 ml). The extract was washed with an aqueous solution of sodium bicarbonate, dried and concentrated. The residue (5 g) was purified by column chromatography on silica gel (120 g) eluting with a mixture of toluene and ethyl acetate (20:1), and recrystallized from ethanol to afford yellow crystals of 4'-acetyl-2'-(2,4-difluorobenzoyl)methanesulfonanilide (1.5 g).

Workup

  1. temperaturewas refluxed for 4 hours
  2. extractionextracted with ethyl acetate (100 ml)
  3. washThe extract was washed with an aqueous solution of sodium bicarbonate
  4. customdried
  5. concentrationconcentrated
  6. customThe residue (5 g) was purified by column chromatography on silica gel (120 g)
  7. washeluting with a mixture of toluene and ethyl acetate (20:1)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-94b96d0a314146c3bb740f6244f26e05
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

Loading…