m-Chloroperbenzoic acid → HCID 86607028, compound

HRID 1293460Notes

Reaction equation

HRID 1293460 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][CH2:24][CH:25]3[CH2:27][CH2:26]3)=[CH:12][CH:11]=2)=[O:9])=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:36])C=1>C(Cl)(Cl)Cl>[N:1]1[CH:2]=[CH:3][C:4]([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:5][CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10428473HCID 10428473, compound

Product 1

HCID 86607028HCID 86607028, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of N-(pyrid-4-yl)-4-cyclopropylmethoxy-dibenzo[b,d]furan-1-carboxamide (50 mg, 0.139 mmol) (example 28) and m-chloroperbenzoic acid (50-55%) (120 mg, 0.698 mmol) in chloroform (10 ml) was stirred at room temperature for 12-16 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 25 mg of N-(pyrid-4-yl)-4-cyclopropylmethoxy-dibenzo[b,d]furan-1-carboxamide-N1-oxide as white solid; mp: 266-268° 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-31634fb809c64289ac578c5518adef63
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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