Methanol → 2-[[(3-Methyl-2-pyridyl)methyl]sulphinyl]-5-(trifluoromethyl)benzimidazole

HRID 35481Notes

Reaction equation

HRID 35481 reaction equation
[CH3:1][C:2]1[C:3]([CH2:8][S:9][C:10]2[NH:11][C:12]3[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:13]=3[N:14]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C[OH:24]>C(Cl)Cl>[CH3:1][C:2]1[C:3]([CH2:8][S:9]([C:10]2[NH:11][C:12]3[CH:18]=[C:17]([C:19]([F:22])([F:20])[F:21])[CH:16]=[CH:15][C:13]=3[N:14]=2)=[O:24])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 212958642-[[(3-Methyl-2-pyridyl)methyl]thio]-5-(trifluoromethyl)benzimidazole

Product 1

HCID 212959192-[[(3-Methyl-2-pyridyl)methyl]sulphinyl]-5-(trifluoromethyl)benzimidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.7 g of 2-[[(3-methyl-2 -pyridyl)methyl]thio]-5-(trifluoromethyl)benzimidazole are dissolved in 250 ml of methylene chloride and 20 ml of methanol and then cooled to -20°. 4.7 g of m-chloroperbenzoic acid, recrystallized from methylene 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 100 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-[[(3-methyl-2-pyridyl)methyl]sulphinyl]-5 -(trifluoromethyl)benzimidazole of melting point 156°-158°.

Workup

  1. custom4.7 g of m-chloroperbenzoic acid, recrystallized from methylene chloride/petroleum ether
  2. additionare then introduced within 10 minutes
  3. additionpoured into a mixture of 100 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-36f539df287c4cb6b695965756d6b25c
Source dataset
uspto-grants-1988_08
Patent number
US04766133

Reaction notes

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