m-Chloroperbenzoic acid → HCID 21105691, compound

HRID 746443Notes

Reaction equation

HRID 746443 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:30])[C:7]=1[NH:8][C:9]([C:11]1[C:19]2[C:18]3[CH:20]=[C:21]([NH:24][C:25](=[O:27])[CH3:26])[CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14]([O:28][CH3:29])=[CH:13][CH:12]=1)=[O:10].ClC1C=CC=C(C(OO)=[O:39])C=1>ClCCl>[Cl:30][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[NH+:8]([O-:39])[C:9]([C:11]1[C:19]2[C:18]3[CH:20]=[C:21]([NH:24][C:25](=[O:27])[CH3:26])[CH:22]=[CH:23][C:17]=3[O:16][C:15]=2[C:14]([O:28][CH3:29])=[CH:13][CH:12]=1)=[O:10]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11236119HCID 11236119, compound

Product 1

HCID 21105691HCID 21105691, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(3,5-dichloropyrid-4-yl)-4-methoxy-8-acetamido-dibenzo[b,d]furan-1-carboxamide (0.215 gm, 0.49 mmole) (Example 4) was suspended in dichloromethane. To this reaction mixture was added 0.507 gm (2.9 mmoles) of meta-chloroperbenzoic acid (50%) and reaction mixture was refluxed for 3 hours and stirred at room temp. for 12 hours. Dichloromethane was removed under vaccum and the crude compound was purified through silica gel column to obtain 0.066 gm (30%) of the N-oxide.

Workup

  1. additionTo this reaction mixture was added
  2. temperaturewas refluxed for 3 hours
  3. customDichloromethane was removed under vaccum
  4. customthe crude compound was purified through silica gel column

Sources & evidence

ORD record
ord-85ff60f4d7744ad4a0df01f861bc90ce
Source dataset
uspto-grants-2008_07
Patent number
US07393846B2

Reaction notes

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