Hydrochloric Acid → N-(2-Fluoro-4-iodophenyl)methanesulfonamide

HRID 656266Notes

Reaction equation

HRID 656266 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH2:9].N1C=CC=CC=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18].Cl>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:17]([CH3:16])(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 1856942-Fluoro-4-iodoaniline

Product 1

HCID 19785608N-(2-Fluoro-4-iodophenyl)methanesulfonamideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-fluoro-4-iodophenylamine (1.50 g) was dissolved in dichloromethane (40 ml) and to the solution were added pyridine (1.02 ml) and methanesulfonylchloride (700 μl). The mixture was stirred at room temperature for 1 hour and 1.5 N aqueous hydrochloric acid was added thereto to quench the reaction. The resulting mixture was extracted with dichloromethane, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was column-chromatographed (ethyl acetate/hexane=1/1) to yield the compound 3-2 (1.89 g, 95%).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe resulting mixture was extracted with dichloromethane
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was column-chromatographed (ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-e456631fb3dd416e8419fec0356e2fa2
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Reaction notes

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