Methyl iodide → 1H-benzimidazole, 1-methyl-2-(methylsulfonyl)-

HRID 1886042Notes

Reaction equation

HRID 1886042 reaction equation
[CH3:1][S:2]([C:5]1[NH:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[N:6]=1)(=[O:4])=[O:3].[H-].[Na+].I[CH3:17]>CN(C=O)C>[CH3:1][S:2]([C:5]1[N:6]([CH3:17])[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3035262-(methylsulfonyl)-1H-benzimidazole

Product 1

HCID 6407151H-benzimidazole, 1-methyl-2-(methylsulfonyl)-Yield 88.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of 2-(methylsulfonyl)-1H-benzimidazole (4.60 g, 0.023 mol) in DMF (25 mL) was added NaH (60% dispersion in mineral oil; 0.94 g, 0.023 mol) in several portions. After 1 hour, iodomethane (3.33 g, 0.023 mol) was added. The cooling bath was removed and stirring was continued for 18 hours. The mixture was recooled to 0° C., H2O (75 mL) was added, and the off-white precipitate was collected by filtration to give 4.30 g (88%) of product m.p. 131°-132° C.

Workup

  1. customThe cooling bath was removed
  2. waitwas continued for 18 hours
  3. customwas recooled to 0° C.
  4. additionH2O (75 mL) was added
  5. filtrationthe off-white precipitate was collected by filtration

Sources & evidence

ORD record
ord-0331452ae5cb4b1683b71b525695cc46
Source dataset
uspto-grants-1992_09
Patent number
US05149700

Reaction notes

Loading…