m-Chloroperbenzoic acid → HCID 10021071, compound

HRID 2418243Notes

Reaction equation

HRID 2418243 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[F:12][C:13]([F:34])([F:33])[C:14]1[C:22]2[N:21]=[C:20]([S:23][CH2:24][C:25]3[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][N:26]=3)[NH:19][C:18]=2[CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[F:34][C:13]([F:33])([F:12])[C:14]1[C:22]2[N:21]=[C:20]([S:23]([CH2:24][C:25]3[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][N:26]=3)=[O:6])[NH:19][C:18]=2[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 100200714-trifluoromethyl-2-[(4-methoxy-2-pyridylmethyl)thio]-(1H)-benzimidazole

Product 1

HCID 10021071HCID 10021071, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.3 g of commercially available 85% strength m-chloroperoxybenzoic acid, dissolved in 30 ml of methylene chloride, are added dropwise to a solution, cooled to -30° C., of 3.0 g (0.0088 mole) of 4-trifluoromethyl-2-[(4-methoxy-2-pyridylmethyl)thio]-(1H)-benzimidazole in 50 ml of methylene chloride over the course of 45 minutes. The resulting mixture is then stirred for a further 60 minutes, and the temperature is subsequently allowed to rise to 0° C. After the mixture is washed with saturated aqueous sodium carbonate solution (30 ml), it is dried over sodium sulfate, and the solvent is stripped off in vacuo. The solid residue which remains is recrystallized successively from isopropanol and acetonitrile. Yield: 1.6 g of title compound, m.p. 150° to 151° C.

Workup

  1. additionare added dropwise to a solution
  2. customto rise to 0° C
  3. washAfter the mixture is washed with saturated aqueous sodium carbonate solution (30 ml), it
  4. dry with materialis dried over sodium sulfate
  5. customThe solid residue which remains is recrystallized successively from isopropanol and acetonitrile

Sources & evidence

ORD record
ord-ac2e7237c81246a6ac20aa78dcce5ef7
Source dataset
uspto-grants-1984_09
Patent number
US04472409

Reaction notes

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