Hydrochloric Acid → N-(3,5-Difluoro-4-iodopyridin-2-yl)propane-1-sulfonamide

HRID 710572Notes

Reaction equation

HRID 710572 reaction equation
[F:1][C:2]1[C:3]([N:10](S(CCC)(=O)=O)[S:11]([CH2:14][CH2:15][CH3:16])(=[O:13])=[O:12])=[N:4][CH:5]=[C:6]([F:9])[C:7]=1[I:8].Cl>[OH-].[Na+]>[F:1][C:2]1[C:3]([NH:10][S:11]([CH2:14][CH2:15][CH3:16])(=[O:13])=[O:12])=[N:4][CH:5]=[C:6]([F:9])[C:7]=1[I:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67366767N-(3,5-Difluoro-4-iodopyridin-2-yl)-N-(propylsulfonyl)propane-1-sulfonamide

Product 1

HCID 86686187N-(3,5-Difluoro-4-iodopyridin-2-yl)propane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Crude N-(3,5-Difluoro-4-iodopyridin-2-yl)-N-(propylsulfonyl)propane-1-sulfonamide (obtained in Step 1) was stirred with 5% aqueous sodium hydroxide solution (20 ml) at 60° C. for 1 h. The cooled reaction mixture was then acidified with 10% hydrochloric acid to pH<2 and extracted with DCM. The combined extracts were dried over sodium sulfate, filtered, and concentrated. The residue was chromatographed on silica gel (20-30% ethyl acetate in hexanes eluant) to provide the title compound. MS m/z 363.1 (M+1).

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with DCM
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (20-30% ethyl acetate in hexanes eluant)

Sources & evidence

ORD record
ord-07c72adc46f04d1a829582da38132b7b
Source dataset
uspto-grants-2015_11
Patent number
US09181238B2

Reaction notes

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