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

HRID 1030281Notes

Reaction equation

HRID 1030281 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S: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][S: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 19822356N-[4-(3-chloro-1-propylthio)phenyl]methanesulfonamide

Product 1

HCID 19822344N-[4-(3-Iodo-1-propylthio)phenyl]methanesulfonamideYield 92.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of N-[4-(3-chloro-1-propylthio)phenyl]methanesulfonamide (4.0 g, 0.014 mol) and sodium iodide (6.4 g 0.043 mol) in acetone (55 mL) was heated under reflux for 18 hours. The mixture was concentrated, taken up in EtOAc, washed with brine, 10% aqueous sodium bisulfite, brine, dried (MgSO4), and concentrated to give 4.8 g (91%) of product as an off-white and solid m.p. 59°-63° C.

Workup

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

Sources & evidence

ORD record
ord-540777f297874d6fa14279382e7667f3
Source dataset
uspto-grants-1992_04
Patent number
US05104892

Reaction notes

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