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

HRID 1962315Notes

Reaction equation

HRID 1962315 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-3d9f19e0ab884101882221c14d22c05b
Source dataset
uspto-grants-2013_04
Patent number
US08415351B2

Reaction notes

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