Methanol → 2-[[(4-Methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

HRID 35477Notes

Reaction equation

HRID 35477 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([CH2:10][S:11][C:12]2[NH:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)[C:4]=1[CH3:21].C[OH:23]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([CH2:10][S:11]([C:12]2[NH:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[N:13]=2)=[O:23])[C:4]=1[CH3:21]

Participants

4

Reactant 2

HCID 887MethanolHCID 106618911H-Benzimidazole, 2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio]-

Product 1

HCID 99487972-[[(4-Methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

53.5 g of 2-[[(4-methoxy-3,5-dimethyl-2 -pyridyl)methyl]thio]benzimidazole are dissolved in 1.2 l of methylene chloride and 100 ml of methanol and then cooled to -20°. 33.4 g of m-chloroperbenzoic acid, recrystallized from methylene chloride/petroleum ether, are then introduced within 10 minutes. The solution is stirred for a further 60 minutes at -20° and then poured into a mixture of 250 ml of 2N sodium carbonate solution and ice. The organic phase is washed neutral with water, dried over sodium sulphate and evaporated in vacuo. Crystallization from methylene chloride/methanol/petroleum ether gives 2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulphinyl]benzimidazole of melting point 157°-159°.

Workup

  1. custom33.4 g of m-chloroperbenzoic acid, recrystallized from methylene chloride/petroleum ether
  2. additionare then introduced within 10 minutes
  3. additionpoured into a mixture of 250 ml of 2N sodium carbonate solution and ice
  4. washThe organic phase is washed neutral with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo
  7. customCrystallization from methylene chloride/methanol/petroleum ether

Sources & evidence

ORD record
ord-66486602e76b4c40829475e0d92f3822
Source dataset
uspto-grants-1988_08
Patent number
US04766133

Reaction notes

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