m-Chloroperbenzoic acid → HCID 86620985, compound

HRID 1293462Notes

Reaction equation

HRID 1293462 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:28])[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][CH:25]([CH3:27])[CH3:26])=[CH:13][CH:12]=1)=[O:10].ClC1C=CC=C(C(OO)=[O:37])C=1>C(Cl)(Cl)Cl>[Cl:28][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[NH+:8]([O-:37])[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][CH:25]([CH3:26])[CH3:27])=[CH:13][CH:12]=1)=[O:10]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10454496HCID 10454496, compound

Product 1

HCID 86620985HCID 86620985, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of N-(3,5-dichloropyrid-4-yl)-4-isopropyloxy-dibenzo[b,d]furan-1-carboxamide (60 mg, 0.144 mmol) (example 32) and m-chloroperbenzoic acid (50-55%) (120 mg, 0.722 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 30% acetone-chloroform as the eluent to give 57 mg of N-(3,5dichlorpyrid-4-yl)-4-isopropyloxy-dibenzo[b,d]furan-1-carboxamide-N1-oxide as white solid; mp: 247-248° 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-68731515278b45e78bfdc785da4b790f
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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