N-Iodosuccinimide → 2-Iodo-4-[(methylsulfonyl)methyl]benzenamine

HRID 633586Notes

Reaction equation

HRID 633586 reaction equation
[CH3:1][S:2]([CH2:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1)(=[O:4])=[O:3].[I:13]N1C(=O)CCC1=O>CN(C)C=O>[I:13][C:11]1[CH:12]=[C:6]([CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])[CH:7]=[CH:8][C:9]=1[NH2:10]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 128439644-[(methylsulfonyl)methyl]aniline(SALTDATA: FREE)

Product 1

HCID 193717842-Iodo-4-[(methylsulfonyl)methyl]benzenamineYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 110B (1.117 g, 6.03 mmol) in dimethylformamide (60.3 mL) was added N-iodosuccinimide (1.492 g, 6.63 mmol). The reaction mixture was stirred at room temperature for 90 minutes. The reaction mixture was quenched with 10% sodium thiosulfate and saturated aqueous sodium bicarbonate and extracted with ethyl acetate three times. The combined organic layers were washed with saturated aqueous sodium chloride, dried with anhydrous magnesium sulfate, filtered, and concentrated. Water was added to the residue, and the mixture was stirred at room temperature for 10 minutes and filtered to give the title compound (1.55 g, 83%).

Workup

  1. customThe reaction mixture was quenched with 10% sodium thiosulfate and saturated aqueous sodium bicarbonate
  2. extractionextracted with ethyl acetate three times
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionWater was added to the residue
  8. stirringthe mixture was stirred at room temperature for 10 minutes
  9. filtrationfiltered

Sources & evidence

ORD record
ord-4b1cb559513344b4a0eff51a0d23349e
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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