m-Chloroperbenzoic acid → HCID 86607026, compound

HRID 1293459Notes

Reaction equation

HRID 1293459 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:29])[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][CH2:25][CH:26]2[CH2:28][CH2:27]2)=[CH:13][CH:12]=1)=[O:10].ClC1C=CC=C(C(OO)=[O:38])C=1>C(Cl)(Cl)Cl>[Cl:29][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[NH+:8]([O-:38])[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][CH2:25][CH:26]2[CH2:27][CH2:28]2)=[CH:13][CH:12]=1)=[O:10]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10410248HCID 10410248, compound

Product 1

HCID 86607026HCID 86607026, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of N-(3,5-dichloropyrid-4-yl)-4-cyclopropylmethoxy-dibenzo[b,d]furan-1-carboxamide (370 mg, 0.936 mmol) (example 26) and m-chloroperbenzoic acid (50-55%) (1.0 gm, 4.68 mmol) in chloroform (20 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 30% acetone-chloroform as the eluent to give 200 mg of N-(3,5-dichloropyrid-4-yl)-4-cyclopropylmethoxy-dibenzo[b,d]furan-1-carboxamide-N1-oxide as white solid; mp: 263-265° 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-59e335efc62042f3b45c3b11d03863fb
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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