Triethylamine → N-(2-iodophenyl)methanesulfonamide

HRID 985718Notes

Reaction equation

HRID 985718 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[I:6][C:7]1[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=1[NH2:9].C(N(CC)CC)C>ClCCl>[I:6][C:7]1[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=1[NH:9][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 119952-IodoanilineHCID 31297Methanesulfonyl chloride

Product 1

HCID 780001N-(2-iodophenyl)methanesulfonamideYield 75.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (4.4 mL, 57 mmol) was added to a 0° C. dichloromethane (200 mL) solution containing 2-iodoaniline (5.0 g, 23 mmol) and triethylamine (9.6 mL, 69 mmol). The resulting mixture was stirred for 90 minutes, washed with HCl (0.5 M). The organics were separated then dried over sodium sulfate and concentrated in vacuo. The residue was then treated with potassium hydroxide (2.0 M in 1:1 methanol:water, 75 mL) for 30 min. This material was then diluted with dichloromethane and washed with HCl (1.0 N, 300 mL). The organics were separated then dried over sodium sulfate and concentrated to provide the title compound (5.15 g) as a tan solid.

Workup

  1. washwashed with HCl (0.5 M)
  2. customThe organics were separated
  3. dry with materialthen dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. additionThe residue was then treated with potassium hydroxide (2.0 M in 1:1 methanol:water, 75 mL) for 30 min
  6. additionThis material was then diluted with dichloromethane
  7. washwashed with HCl (1.0 N, 300 mL)
  8. customThe organics were separated
  9. dry with materialthen dried over sodium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-6a22d669e1cf487c81ae823682ef95a2
Source dataset
uspto-grants-2005_03
Patent number
US06872834B2

Reaction notes

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