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

HRID 874437Notes

Reaction equation

HRID 874437 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 3b (1.12 g, 6.03 mmol) in dimethylformamide (60.3 mL) was added N-iodosuccinimide (1.49 g, 6.63 mmol). The reaction mixture was stirred at ambient 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 ambient 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 ambient temperature for 10 minutes
  9. filtrationfiltered

Sources & evidence

ORD record
ord-443f5fdced4147faa789ad6294845751
Source dataset
uspto-grants-2015_03
Patent number
US08980879B2

Reaction notes

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