m-Chloroperbenzoic acid → HCID 86607030, compound

HRID 1293461Notes

Reaction equation

HRID 1293461 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][CH2:24][CH:25]3[CH2:27][CH2:26]3)=[CH:12][CH:11]=2)=[O:9])[CH:2]=1.ClC1C=CC=C(C(OO)=[O:36])C=1>C(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH+:7]([O-:36])[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][CH2:24][CH:25]3[CH2:27][CH2:26]3)=[CH:12][CH:11]=2)=[O:9])[CH:2]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10473572HCID 10473572, compound

Product 1

HCID 86607030HCID 86607030, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of N-(pyrid-3-yl)-4-cyclopropylmethoxy-dibenzo[b,d]furan-1-carboxamide (15 mg, 0.139 mmol) (example 30) and m-chloroperbenzoic acid (50-55%) (120 mg, 0.698 mmol) in chloroform (10 ml) was stirred at room temperature for 12 h. The reaction contents were washed with saturated sodium bicarbonate and water. The organic solvent was distilled of in vacuo and the residue was purified by column chromatography using 40% acetone-chloroform as the eluent to give 30 mg of N-(pyrid-3-yl)-4-cyclopropylmethoxy-dibenzo[b,d]furan-1-carboxamide-N-oxide as white solid; mp: 272-275° C.

Workup

  1. customThe reaction contents
  2. washwere washed with saturated sodium bicarbonate and water
  3. distillationThe organic solvent was distilled of in vacuo
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-624b922c724e402b96d46680bb1efe1f
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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