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

HRID 1261023Notes

Reaction equation

HRID 1261023 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH2:9].C(N(CC)CC)C.[CH2:17]([S:20](Cl)(=[O:22])=[O:21])[CH2:18][CH3:19].Cl>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:20]([CH2:17][CH2:18][CH3:19])(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 97092,4-DifluoroanilineHCID 662791-Propanesulfonyl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2,4-difluoro-phenylamine (42, 3.0 mL, 29.8 mmol) in tetrahydrofuran (50 mL) were added triethylamine (9.13 mL, 65.5 mmol) and propane-1-sulfonyl chloride (2.90 mL, 25.8 mmol) under an atmosphere of nitrogen. The reaction was stirred at room temperature overnight. The reaction was poured into 1 M HCl and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to give the compound (72, 2.0 g, 28%) that was used in the next step.

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. customto give the compound (72, 2.0 g, 28%) that

Sources & evidence

ORD record
ord-b7413f61231247f2b7dd80e2f7a8d4b9
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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