m-Chloroperbenzoic acid → HCID 86607018, compound

HRID 1293454Notes

Reaction equation

HRID 1293454 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:26])[C:7]=1[NH:8][C:9]([C:11]1[C:19]2[C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14]([O:24][CH3:25])=[CH:13][CH:12]=1)=[O:10].ClC1C=CC=C(C(OO)=[O:35])C=1>C(Cl)(Cl)Cl>[Cl:26][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[NH+:8]([O-:35])[C:9]([C:11]1[C:19]2[C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14]([O:24][CH3:25])=[CH:13][CH:12]=1)=[O:10]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 98431931-Dibenzofurancarboxamide, N-(3,5-dichloro-4-pyridinyl)-4-methoxy-

Product 1

HCID 86607018HCID 86607018, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of N-(3,5-dichloropyrid-4-yl)-4-methoxy dibenzo[b,d]furan-1-carboxamide (200 mg, 0.518 mmol) (example 1) and m-chloroperbenzoic acid (50-55%) (880 mg, 2.5 mmol) in chloroform (10 ml) was refluxed for 2 h. The reaction was cooled and washed with saturated sodium bicarbonate and water. The organic solvent was distilled of in vacuo and the residue was purified by column chromatography using 20% acetone-chloroform as the eluent to give 150 mg of N-(3,5-dichloropyrid-4-yl)-4-methoxy dibenzo[b,d]furan-1-carboxamide-N1-oxide as white solid; mp: 265-270° C.

Workup

  1. temperaturewas refluxed for 2 h
  2. temperatureThe reaction was cooled
  3. washwashed with saturated sodium bicarbonate and water
  4. distillationThe organic solvent was distilled of in vacuo
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-7aac8013dd5e4e94b8ae21f83c7b0156
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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