Water → N-(2,4-difluoro-3-formylphenyl)propane-2-sulfonamide

HRID 1098376Notes

Reaction equation

HRID 1098376 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11].C([Li])CCC.CN(C)[CH:23]=[O:24].O>O1CCCC1>[F:1][C:2]1[C:7]([CH:23]=[O:24])=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 58087510N-(2,4-difluorophenyl)propane-2-sulfonamideHCID 178418339Butyllithium2×

Product 1

HCID 58086031N-(2,4-difluoro-3-formylphenyl)propane-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To propane-2-sulfonic acid (2,4-difluoro-phenyl)-amide (59, 2.35 g, 9.95 mmol) in tetrahydrofuran (70 mL) under an atmosphere of nitrogen cooled with a dry ice/acetone bath was added 1.60 M of n-butyllithium (1.60 M in hexane, 6.53 mL, 10.45 mmol). The reaction was stirred for 40 minutes, and then another portion of n-butyllithium (1.60 M in hexane, 6.84 mL, 10.94 mmol). The reaction was stirred for 1 hour and N,N-dimethylformamide (0.92 mL, 11.9 mmol) was added. The reaction was allowed to warm to room temperature overnight. The reaction was poured into water extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtrated. The filtrate was concentrated and purified by silica gel column chromatography (dichloromethane/methanol 5%) to give the compound (60, 1.4 g, 53.4%). MS (ESI) [M−H+]−=263.4.

Workup

  1. stirringThe reaction was stirred for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltrated
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography (dichloromethane/methanol 5%)
  8. customto give the compound (60, 1.4 g, 53.4%)

Sources & evidence

ORD record
ord-a919715947de42f299981fe05f9104e9
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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