Formic Acid → HCID 9997539, compound

HRID 1087223Notes

Reaction equation

HRID 1087223 reaction equation
[C:1]([C:3]1[CH:13]=[CH:12][C:6]([NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[C:5]([S:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])[CH:4]=1)#N.C(O)=[O:24]>[Ni]>[F:22][C:16]1[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:15]=1[S:14][C:5]1[CH:4]=[C:3]([CH:1]=[O:24])[CH:13]=[CH:12][C:6]=1[NH:7][S:8]([CH3:11])(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 10404983HCID 10404983, compound

Product 1

HCID 9997539HCID 9997539, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A mixture of 4'-cyano-2'-(2,4-difluorophenylthio)methanesulfonanilide (4.8 g) and Raney's Nickel (4.8 g) in 75% formic acid (130 ml) was stirred and refluxed for 2 hours. The mixture was filtered and the filtrate was concentrated to dryness. The residue was dissolved in chloroform, washed with an aqueous solution of sodium bicarbonate, dried and evaporated. The oily residue (5 g) was purified by column chromatography on silica gel (100 g) eluting with a mixture of toluene and ethyl acetate (5:1) to give crystals of 2'-(2,4-difluorophenylthio)-4'-formylmethanesulfonanilide (3.0 g).

Workup

  1. temperaturerefluxed for 2 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated to dryness
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with an aqueous solution of sodium bicarbonate
  6. customdried
  7. customevaporated
  8. customThe oily residue (5 g) was purified by column chromatography on silica gel (100 g)
  9. washeluting with a mixture of toluene and ethyl acetate (5:1)

Sources & evidence

ORD record
ord-170ac3ba79d14f20be5c3ac40c156695
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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