Methyl iodide → 3-Methyl-1-[2-[4-((methylsulfonyl)amino)phenyl]ethyl]-1H-imidazolium iodide

HRID 1789480Notes

Reaction equation

HRID 1789480 reaction equation
[N:1]1([CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[I:19][CH3:20]>CO>[I-:19].[CH3:20][N:3]1[CH:4]=[CH:5][NH+:1]([CH2:6][CH2:7][C:8]2[CH:9]=[CH:10][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:12][CH:13]=2)[CH2:2]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 137633971-[2-[4-[(Methylsulfonyl)amino]phenyl]ethyl]-1H-imidazole

Product 1

HCID 704378243-Methyl-1-[2-[4-((methylsulfonyl)amino)phenyl]ethyl]-1H-imidazolium iodide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Heat a mixture of 5 g (0.019 mole) of N-[4-[2-(1H-imidazol-1-yl)ethyl]phenyl]methanesulfonamide, 5 mL of iodomethane and 25 mL of methanol in a pressure tube at 75° C. for about 24 hours. Cool the mixture to room temperature and remove the solvents in vacuo. Slurry the residue in acetone (50 mL) and filter and wash with acetone (100 mL). Drying provides the title compound, which may be recrystallized from methanol.

Workup

  1. temperatureHeat
  2. customremove the solvents in vacuo
  3. filtrationfilter
  4. washwash with acetone (100 mL)
  5. customDrying

Sources & evidence

ORD record
ord-fe6bc469579849c190d98ec39f6d6c77
Source dataset
uspto-grants-1987_08
Patent number
US04689341

Reaction notes

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