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

HRID 1397837Notes

Reaction equation

HRID 1397837 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].Cl>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 313Hydrochloric AcidHCID 1049PyridineHCID 97092,4-DifluoroanilineHCID 662791-Propanesulfonyl chloride

Product 1

HCID 53419004N-(2,4-Difluorophenyl)propane-1-sulfonamideYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2,4-difluoro-phenylamine (1, 11.8 g, 91.4 mmol) in 110 mL of dichloromethane, pyridine (8.13 mL, 100 mmol) and propane-1-sulfonyl chloride (4, 11.3 mL, 100 mmol) were added. The reaction was stirred at room temperature overnight, then poured into 1 M aqueous hydrochloric acid, the aqueous layer separated and extracted with ethyl acetate. The organic layers were combined and washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum. The crude material was purified by silica gel column chromatography to give the desired compound (11, 19.98 g, 92.9%). MS(ESI)=[M−H+]−=234.06.

Workup

  1. customthe aqueous layer separated
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under vacuum
  7. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4f9f8830629e4116aebdd205de3b5448
Source dataset
uspto-grants-2014_12
Patent number
US08901301B2

Reaction notes

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