m-Chloroperbenzoic acid → HCID 86607022, compound

HRID 1293457Notes

Reaction equation

HRID 1293457 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]([C:10]2[C:18]3[C:17]4[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=4[O:15][C:14]=3[C:13]([O:23][CH:24]([F:26])[F:25])=[CH:12][CH:11]=2)=[O:9])=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:35])C=1>C(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][C:4]([NH+:7]([O-:35])[C:8]([C:10]2[C:18]3[C:17]4[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=4[O:15][C:14]=3[C:13]([O:23][CH:24]([F:26])[F:25])=[CH:12][CH:11]=2)=[O:9])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10450770HCID 10450770, compound

Product 1

HCID 86607022HCID 86607022, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of N-(pyrid-4-yl)-4-difluoromethoxy-dibenzo[b,d]furan-1-carboxamide (50 mg, 0.14 mmol) (example 21) and m-chloroperbenzoic acid (50-55%) (120 mg, 0.70 mmol) in chloroform (10 ml) was stirred at room temperature for 16 h. Chloroform was evaporated and the resulting solid was stirred in saturated sodium bicarbonate solution, filtered, dried and purified by column chromatography using 40% acetone-chloroform as the eluent to give 30 mg of N-(pyrid-4-yl)-4-difluoromethoxy-dibenzo[b,d]furan-1-carboxamide-N1-oxide as white solid; mp: 244° C.

Workup

  1. customChloroform was evaporated
  2. stirringthe resulting solid was stirred in saturated sodium bicarbonate solution
  3. filtrationfiltered
  4. customdried
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-41f84041a6e044c9a9f5bccebc5e14a0
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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