Sodium Iodide → N-[4-(3-Iodo-1-propyloxy)phenyl]methanesulfonamide

HRID 1030276Notes

Reaction equation

HRID 1030276 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][CH:7]=1.[I-:17].[Na+]>CC(C)=O>[I:17][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 19822347N-[4-(3-Chloro-1-propyloxy)phenyl]methanesulfonamide

Product 1

HCID 19822359N-[4-(3-Iodo-1-propyloxy)phenyl]methanesulfonamideYield 96.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of N-[4-(3-chloro-1-propyloxy)phenyl]methanesulfonamide (1.03 g, 3.90 mmol) and sodium iodide (1.75 g, 11.70 mmol) in acetone (15 mL) was heated under reflux for 18 hours. The mixture was concentrated, taken up in EtOAc, and washed with brine, 10% aqueous sodium bisulfite, and brine. The organic phase was dried (MgSO4) and concentrated to give 1.34 g (96%) of product as an off-white solid m.p. 109°-111° C.

Workup

  1. temperatureunder reflux for 18 hours
  2. concentrationThe mixture was concentrated
  3. washwashed with brine, 10% aqueous sodium bisulfite, and brine
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b9c2efe2389f4fba86b97cbb3cda15c3
Source dataset
uspto-grants-1992_04
Patent number
US05104892

Reaction notes

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