Ammonium Chloride → N-(2-iodo-4-nitrophenyl)-N-(methylsulfonyl)methanesulfonamide

HRID 541076

Reaction equation

HRID 541076 reaction equation
[I:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:12][S:13](Cl)(=[O:15])=[O:14].[NH4+].[Cl-]>ClCCl>[I:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[N:4]([S:13]([CH3:12])(=[O:15])=[O:14])[S:13]([CH3:12])(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 2226292-Iodo-4-nitroaniline

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-iodo-4-nitroaniline (1.02 g, 3.86 mmol) in dichloromethane (10 ml), has been added under stirring triethylamine (1.77 ml, 12.7 mmol). To this mixture, a solution of methanesulphonyl chloride (0.98 ml, 12.7 mmol) in dichloromethane (2 ml) has been added dropwise, very slowly and in an ice-bath. The mixture so obtained was left under stirring at room temperature overnight. The day after, the reaction mixture was neutralized with a saturated aqueous solution of NH4Cl. The organic phase was separated, and, after evaporation of the solvent, the residue has been washed with ethanol and filtered to give N-(2-iodo-4-nitrophenyl)-N-(methylsulfonyl)-methanesulfonamide as yellow solid.

Workup

  1. customThe mixture so obtained
  2. waitwas left
  3. customThe organic phase was separated
  4. customafter evaporation of the solvent
  5. washthe residue has been washed with ethanol
  6. filtrationfiltered

Sources & evidence

ORD record
ord-23c8accabf5148f295a6c4c2ee2b86d0
Source dataset
uspto-grants-2014_10
Patent number
US08871948B2

Linked notes

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