m-Chloroperbenzoic acid → HCID 86607020, compound

HRID 1293456Notes

Reaction equation

HRID 1293456 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][CH3:24])=[CH:12][CH:11]=2)=[O:9])[CH:2]=1.ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH+:7]([O-:33])[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][CH3:24])=[CH:12][CH:11]=2)=[O:9])[CH:2]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10064459HCID 10064459, compound

Product 1

HCID 86607020HCID 86607020, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of N-(pyrid-3-yl)-4-methoxy dibenzo[b,d]furan-1-carboxamide (50 mg, 0.15 mmol) (example 8) and m-chloroperbenzoic acid (50-55%) (135 mg, 0.78 mmol) in chloroform (10 ml) was stirred at room temperature for 16 h. Chloroform was evaporated and the resulting solid was washed with saturated sodium bicarbonate solution, water, dried and then purified by column chromatography using 20% acetone-chloroform as the eluent to give 15 mg of N-(pyrid-3-yl)-4-methoxy dibenzo[b,d]furan-1-carboxamide-N1-oxide as white solid; mp: 239-241° C.

Workup

  1. customChloroform was evaporated
  2. washthe resulting solid was washed with saturated sodium bicarbonate solution, water
  3. customdried
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-5df6e4b002e345d59014b220c66d792f
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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