m-Chloroperbenzoic acid → HCID 10811423, compound

HRID 395733Notes

Reaction equation

HRID 395733 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([C:7]([NH:9][C:10]2[C:11]([NH:16][C:17](=[O:26])[C:18]3[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][CH:19]=3)=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1.ClC1C=C(C=CC=1)C(OO)=[O:34].[OH-].[Ca+2].[OH-]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[C:11]([NH:16][C:17](=[O:26])[C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:25])=[O:34])=[CH:20][CH:19]=3)=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 10834358N1-(4-Methoxybenzoyl)-N2-[4-(methylthio)benzoyl]-1,2-benzenediamine

Product 1

HCID 10811423HCID 10811423, compoundYield 146.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of N1-(4-Methoxybenzoyl)-N2-[4-(methylthio)benzoyl]-1,2-benzenediamine (417 mg, 0.60 mmol) in chloroform (20 mL), cooled to 0° C. was added m-chloroperoxybenzoic acid (346 mg, 1.16 mmol). After 30 min, the reaction mixture was warmed to room temperature and calcium hydroxide (123 mg, 1.66 mmol) was added. After 15 min, the reaction mixture was filtered and the filtrate concentrated in vacuo. The residue was chromatographed (silica gel, 50% ethyl acetate/50% hexanes to 80% ethyl acetate/20% hexanes) to give 360 mg (83%) of the title compound as a white solid.

Workup

  1. waitAfter 15 min
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was chromatographed (silica gel, 50% ethyl acetate/50% hexanes to 80% ethyl acetate/20% hexanes)

Sources & evidence

ORD record
ord-7aac4039f3d74b7d88dde86242ca0941
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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