Hydrochloric Acid → N-(2-iodo-4-nitrophenyl)methanesulfonamide

HRID 541077Notes

Reaction equation

HRID 541077 reaction equation
[Li+].[OH-].[I:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[N:13](S(C)(=O)=O)[S:14]([CH3:17])(=[O:16])=[O:15].[NH4+].[Cl-].Cl>C(O)C.O.C(O)C.O>[I:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[NH:13][S:14]([CH3:17])(=[O:16])=[O:15]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 25517Ammonium ChlorideHCID 67284344N-(2-iodo-4-nitrophenyl)-N-(methylsulfonyl)methanesulfonamide

Product 1

HCID 67284366N-(2-iodo-4-nitrophenyl)methanesulfonamide

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

LiOH (0.21 mg, 8.9 mmol) in a mixture ethanol/water 2/1 (18 ml) was added to a solution of N-(2-iodo-4-nitrophenyl)-N-(methylsulfonyl)methanesulfonamide (0.75 g, 1.78 mmol). The reaction mixture was refluxed for two hours. After cooling at room temperature, the reaction mixture was neutralized with H2O, NH4Cl and HCl 2N, then ethanol was eliminated, and the aqueous phase was extracted with ethyl acetate (3×20 ml). The organic solvent was removed by evaporating under reduced pressure to give N-(2-iodo-4-nitrophenyl)methanesulfonamide without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed for two hours
  2. extractionthe aqueous phase was extracted with ethyl acetate (3×20 ml)
  3. customThe organic solvent was removed
  4. customby evaporating under reduced pressure

Sources & evidence

ORD record
ord-46487f4b25c4403296834598b10f9915
Source dataset
uspto-grants-2014_10
Patent number
US08871948B2

Reaction notes

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