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

HRID 1947435Notes

Reaction equation

HRID 1947435 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-58c8e0970a61404b8d55bc347df337aa
Source dataset
uspto-grants-2013_03
Patent number
US08399477B2

Reaction notes

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