Pyridine → N-(2,4-difluorophenyl)propane-2-sulfonamide

HRID 1261017Notes

Reaction equation

HRID 1261017 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH2:9].N1C=CC=CC=1.[CH3:16][CH:17]([S:19](Cl)(=[O:21])=[O:20])[CH3:18].CN(C1C=CC=CN=1)C>C(Cl)Cl.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:19]([CH:17]([CH3:18])[CH3:16])(=[O:21])=[O:20]

Participants

7

Reactant 4

HCID 1049PyridineHCID 97092,4-DifluoroanilineHCID 218852-DimethylaminopyridineHCID 824082-Propanesulfonyl chloride

Product 1

HCID 58087510N-(2,4-difluorophenyl)propane-2-sulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To 2,4-difluoro-phenylamine (42, 4.0 mL, 40.0 mmol) in methylene chloride (50 mL) were added pyridine (3.37 mL, 42.3 mmol), propane-2-sulfonyl chloride (6.00 g, 42.3 mmol) and dimethylaminopyridine (0.20 g, 1.64 mmol) under an atmosphere of nitrogen. The reaction was stirred at 45° C. overnight. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography 3% methanol in methylene chloride to give a white solid (59, 8.0 g, 85%). MS (ESI) [M−H+]−=234.0.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography 3% methanol in methylene chloride
  7. customto give a white solid (59, 8.0 g, 85%)

Sources & evidence

ORD record
ord-a2d3b2c5b3154273a68efa29dd3336fa
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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