Pyridine → N-(4-iodo-3-methylphenyl)methanesulfonamide

HRID 2360022Notes

Reaction equation

HRID 2360022 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].N1C=CC=CC=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)Cl>[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:17]([CH3:16])(=[O:19])=[O:18])=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 27342754-Iodo-3-methylaniline

Product 1

HCID 58798979N-(4-iodo-3-methylphenyl)methanesulfonamideYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-iodo-3-methylaniline (4.37 g, 18.75 mmol) in CH2Cl2 (25 ml) was treated with pyridine (6.07 ml, 75 mmol) followed by drop wise addition of methanesulfonyl chloride (1.607 ml, 20.63 mmol) to give a reddish/orange mixture. The mixture was stirred for 2 h, concentrated and diluted with EtOAc. The EtOAc layer was washed with 1M HCl, water, saturated NaCl, dried (Na2SO4) and filtered. The EtOAc filtrate was treated with activated charcoal for 30 min at 50° C. and filtered through a 10 g silica plug and concentrated to give the title compound as a light yellow solid (5.5 g, 94%).

Workup

  1. customto give a reddish/orange mixture
  2. concentrationconcentrated
  3. additiondiluted with EtOAc
  4. washThe EtOAc layer was washed with 1M HCl, water, saturated NaCl
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. additionThe EtOAc filtrate was treated with activated charcoal for 30 min at 50° C.
  8. filtrationfiltered through a 10 g silica plug
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-09445becf34c49499f76b42a32117034
Source dataset
uspto-grants-2014_04
Patent number
US08685991B2

Reaction notes

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