m-Chloroperbenzoic acid → HCID 71267538, compound

HRID 1505802Notes

Reaction equation

HRID 1505802 reaction equation
[Cl:1][C:2]1[C:3]([CH3:35])=[C:4]([NH:8][C:9]([C:11]2[C:19]3[N:18]=[C:17]([S:20][CH3:21])[NH:16][C:15]=3[CH:14]=[C:13]([NH:22][C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:34])([F:33])[F:32])=[O:24])[CH:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:44])C=1>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([CH3:35])=[C:4]([NH:8][C:9]([C:11]2[C:19]3[N:18]=[C:17]([S:20]([CH3:21])=[O:44])[NH:16][C:15]=3[CH:14]=[C:13]([NH:22][C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:34])([F:32])[F:33])=[O:24])[CH:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 71267470HCID 71267470, compound

Product 1

HCID 71267538HCID 71267538, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(3-chloro-2-methylphenyl)-2-(methylsulfanyl)-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide (26 mg) in THF (3 mL), was added an aqueous solution of m-chloroperbenzoic acid (75%, 12 mg) (1 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate, washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified on column chromatography to yield the titled compound (10 mg) as pale yellow powder.

Workup

  1. washwashed sequentially with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified on column chromatography

Sources & evidence

ORD record
ord-ee9311ab8b7e4c3d8cd266b7b8cf8161
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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