Lithium Hydroxide → N-(2-iodo-4-nitrophenyl)methanesulfonamide

HRID 1947430Notes

Reaction equation

HRID 1947430 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11](S(C)(=O)=O)[S:12]([CH3:15])(=[O:14])=[O:13].[Li+].[OH-]>CCO.O>[I:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67284344N-(2-iodo-4-nitrophenyl)-N-(methylsulfonyl)methanesulfonamide

Product 1

HCID 67284366N-(2-iodo-4-nitrophenyl)methanesulfonamideYield 93.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture containing N-(2-iodo-4-nitrophenyl)-N-(methylsulfonyl)methanesulfonamide (31 g; 75 mmol) in EtOH (230 ml), water (115 ml) and LiOH (9 g; 375 mmol) were added. The reaction mixture was refluxed for 2 hours, then cooled to room temperature, the solvent evaporated under reduced pressure. NH4Cl (saturated solution, 250 ml) was added and the mixture was stirred until a yellow solid precipitated. The crude product was filtered and dried under vacuum to give N-(2-iodo-4-nitrophenyl)methanesulfonamide (24 g) which was used in the following reaction without any further purification.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was refluxed for 2 hours
  3. customthe solvent evaporated under reduced pressure
  4. additionNH4Cl (saturated solution, 250 ml) was added
  5. customprecipitated
  6. filtrationThe crude product was filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-e662e4b30c074796a0a2254fe58bec44
Source dataset
uspto-grants-2013_03
Patent number
US08399477B2

Reaction notes

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