m-Chloroperbenzoic acid → HCID 22712039, compound

HRID 352534Notes

Reaction equation

HRID 352534 reaction equation
[F:1][C:2]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:26](=[O:27])[C:25]3[C:20](=[N:21][CH:22]=[CH:23][CH:24]=3)[C:18]2=[O:19])=[C:13]([CH3:28])[CH:12]=1)([C:7]([F:10])([F:9])[F:8])[C:3]([F:6])([F:5])[F:4].ClC1C=CC=C(C(OO)=[O:37])C=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[F:1][C:2]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:26](=[O:27])[C:25]3[C:20](=[N+:21]([O-:37])[CH:22]=[CH:23][CH:24]=3)[C:18]2=[O:19])=[C:13]([CH3:28])[CH:12]=1)([C:7]([F:9])([F:8])[F:10])[C:3]([F:6])([F:5])[F:4]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 22712035HCID 22712035, compound

Product 1

HCID 22712039HCID 22712039, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 25 ml of chloroform was dissolved 3.1 g of N-[4-(heptafluoro-2-propyl)-2-methylphenyl]pyridine-2,3-dicarboximide, and 5.0 g of m-chloroperbenzoic acid was added thereto at room temperature. After the resulting mixture was stirred at room temperature for 3 hours, a saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed successively with water, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography using ethyl acetate/n-hexane as an eluent, to obtain 820 mg (yield: 84%) of the desired compound.

Workup

  1. additionwas added
  2. customat room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed successively with water
  5. dry with materiala saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-ed773fe8827041d2b180c43eb3603e2e
Source dataset
uspto-grants-2004_06
Patent number
US06747041B1

Reaction notes

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