Acetic Acid → N-(6-iodopyridin-3-yl)methanesulfonamide

HRID 2360024Notes

Reaction equation

HRID 2360024 reaction equation
[I:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:15][S:16](Cl)(=[O:18])=[O:17].C(O)(=O)C>ClCCl>[I:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][S:16]([CH3:15])(=[O:18])=[O:17])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 23205766-Iodopyridin-3-amine

Product 1

HCID 86652124N-(6-iodopyridin-3-yl)methanesulfonamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-iodopyridin-3-amine (1.077 gm, 4.90 mmole) in dichloromethane (40 ml) and pyridine (1.98 ml, 24.49 mmole) at ice bath temperature was added methanesulfonyl chloride (0.401 ml, 2.444 mmole). The mixture was allowed to warm to room temperature and stir four days. The reaction mixture was treated with 5% acetic acid and allowed to stir 20 min at room temperature. The organic phase was washed with water (2×50 ml), dried (MgSO4) and concentrated in vacuo. The residue was slowly added in portions to rapidly stirred water (100 ml) and the resulting solid collected by filtration, washed with water and dried in vacuo to give the title compound (0.7287 g, 49.9%).

Workup

  1. stirringto stir 20 min at room temperature
  2. washThe organic phase was washed with water (2×50 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. additionThe residue was slowly added in portions to rapidly stirred water (100 ml)
  6. filtrationthe resulting solid collected by filtration
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-d9c58bb40ee74d41a507911cbea9de05
Source dataset
uspto-grants-2014_04
Patent number
US08685991B2

Reaction notes

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