Methanol → 2-(methylsulfonyl)-1H-benzimidazole

HRID 1886041Notes

Reaction equation

HRID 1886041 reaction equation
CS[C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.O[O:13][S:14]([O-:16])=O.[K+].[CH3:18]O>O>[CH3:18][S:14]([C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=1)(=[O:16])=[O:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 235392-(Methylthio)benzimidazoleHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 3035262-(methylsulfonyl)-1H-benzimidazoleYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

According to the procedure of B. M. Trost, et al., Tetrahedron Lett., 22 (14), 1287 (1981), to a cooled (0° C.), stirred solution of 2-(methylthio)benzimidazole (14.5 g, 0.088 mol) in MeOH (350 mL) was added a solution of oxone (2 KHSO5.KHSO4.K2SO4 ; 81.6 g, 0.133 mol) in H2O (350 mL) over 10 minutes. The cooling bath was removed after 10 minutes, stirring was continued at room temperature for 5 hours. The MeOH was removed under reduced pressure and the white solid was collected by filtration to give 15.5 g (89%) of product m.p. 200°-202° C.

Workup

  1. customThe cooling bath was removed after 10 minutes
  2. customThe MeOH was removed under reduced pressure
  3. filtrationthe white solid was collected by filtration

Sources & evidence

ORD record
ord-723a5151c3224c8488cb2c639e08ca45
Source dataset
uspto-grants-1992_09
Patent number
US05149700

Reaction notes

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