m-Chloroperbenzoic acid → HCID 86607024, compound

HRID 1293458Notes

Reaction equation

HRID 1293458 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([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:2]=1.ClC1C=CC=C(C(OO)=[O:35])C=1>C(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([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:25])[F:26])=[CH:12][CH:11]=2)=[O:9])[CH:2]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10450771HCID 10450771, compound

Product 1

HCID 86607024HCID 86607024, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of N-(pyrid-3-yl)-4-difluoromethoxy-dibenzo[b,d]furan-1-carboxamide (50 mg, 0.14 mmol) (example 23) and m-chloroperbenzoic acid (50-55%) (120 mg, 0.704 mmol) in chloroform (10 ml) was stirred at room temperature for 12 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 25 mg of of N-(pyrid-3-yl)-4-difluoromethoxy-dibenzo[b,d]furan-1-carboxamide-N1-oxide as white solid; mp: 252° C. (dec)

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-099af7da969b4995814b719150e98db8
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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