Methanol → 2-[[(4-Methoxy-3,5-dimethyl-2-pyridyl)methyl]sulphinyl]-5-(trifluoromethyl)benzimidazole

HRID 35479Notes

Reaction equation

HRID 35479 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]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:15]=3[N:16]=2)[C:4]=1[CH3:25].C[OH:27]>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:13][C:14]3[CH:20]=[C:19]([C:21]([F:23])([F:24])[F:22])[CH:18]=[CH:17][C:15]=3[N:16]=2)=[O:27])[C:4]=1[CH3:25]

Participants

4

Reactant 2

HCID 887MethanolHCID 104290262-[[(4-Methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]-5-(trifluoromethyl)benzimidazole

Product 1

HCID 98863002-[[(4-Methoxy-3,5-dimethyl-2-pyridyl)methyl]sulphinyl]-5-(trifluoromethyl)benzimidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

31.4 g of 2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]-5-(trifluoromethyl)benzimidazole are dissolved in 1.3 l of methylene chloride and 50 ml of methanol and then cooled to -20°. 16.9 g of m-chloroperbenzoic acid, recrystallized from a methyene chloride/petroleum ether, are then introduced within 10 minutes. The solution is stirred further at -20° for 60 minutes and then poured into a mixture of 120 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]-5-(trifluoromethyl)benzimidazole of melting point 152°-154°.

Workup

  1. custom16.9 g of m-chloroperbenzoic acid, recrystallized from a methyene chloride/petroleum ether
  2. additionare then introduced within 10 minutes
  3. additionpoured into a mixture of 120 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-7829d988bc3340d3bea8f2c0b997b908
Source dataset
uspto-grants-1988_08
Patent number
US04766133

Reaction notes

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