m-Chloroperbenzoic acid → 5-Trifluoromethyl-2-methylsulfinyl-benzimidazole

HRID 2418250Notes

Reaction equation

HRID 2418250 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[F:12][C:13]([F:26])([F:25])[C:14]1[CH:24]=[CH:23][C:17]2[N:18]=[C:19]([S:21][CH3:22])[NH:20][C:16]=2[CH:15]=1>C(Cl)Cl>[F:26][C:13]([F:25])([F:12])[C:14]1[CH:24]=[CH:23][C:17]2[N:18]=[C:19]([S:21]([CH3:22])=[O:6])[NH:20][C:16]=2[CH:15]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 204460571H-Benzimidazole, 2-(methylthio)-6-(trifluoromethyl)-

Product 1

HCID 177690195-Trifluoromethyl-2-methylsulfinyl-benzimidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.6 g (0.013 mole) of commercially available 85% strength m-chloroperoxybenzoic acid are added dropwise to a suspension, cooled to -20° C., of 3.0 g (0.013 mole) of 5-trifluoromethyl-2-methylthio-benzimidazole in 50 ml of methylene chloride in the course of 30 minutes. The mixture is then stirred for a further 60 minutes and is then extracted twice with, each time, 20 ml of an aqueous potassium carbonate solution. The solvent is stripped off in vacuo and the solid residue which remains is recrystallized from acetonitrile. 1.8 g of 5-trifluoromethyl-2-methylsulfinyl-benzimidazole of m.p. 135° C. are obtained. Deprotonation of this compound with n-butyllithium and reaction with 2-chloro-4-methoxypyridine in dry benzene yields the title compound of m.p. 166° C. (decomposition).

Workup

  1. extractionis then extracted twice with, each time, 20 ml of an aqueous potassium carbonate solution
  2. customthe solid residue which remains is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-b4fdf4e8138f4af6a17fb705d71dea1f
Source dataset
uspto-grants-1984_09
Patent number
US04472409

Reaction notes

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