Water → N-(2,4-Difluorophenyl)propane-1-sulfonamide

HRID 2387266Notes

Reaction equation

HRID 2387266 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.[CH2:16]([S:19](Cl)(=[O:21])=[O:20])[CH2:17][CH3:18].O>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:19]([CH2:16][CH2:17][CH3:18])(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 97092,4-DifluoroanilineHCID 662791-Propanesulfonyl chloride

Product 1

HCID 53419004N-(2,4-Difluorophenyl)propane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2,4-difluoro-phenylamine (8, 11.8 g, 91.4 mmol) in dichloromethane (110 mL) were added pyridine (8.13 mL, 100 mmol) and propane-1-sulfonyl chloride (11.3 mL. 100 mmol). The reaction was stirred overnight. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with 1M HCl solution and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 10% ethyl acetate in hexane to give a solid (9, 19.98 g, 93%). MS (ESI) [M−H+]−=234.1.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 1M HCl solution and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography
  7. washeluting with 10% ethyl acetate in hexane
  8. customto give a solid (9, 19.98 g, 93%)

Sources & evidence

ORD record
ord-de3bc2b1b81b4b1d93592b2a0cc669c0
Source dataset
uspto-grants-2012_09
Patent number
US08268858B2

Reaction notes

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