m-Chloroperbenzoic acid → HCID 10811423, compound

HRID 427585Notes

Reaction equation

HRID 427585 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-2b8516dcd9b94668a4fb2599b914684d
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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