m-Chloroperbenzoic acid → HCID 22719962, compound

HRID 1582190Notes

Reaction equation

HRID 1582190 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][N:13]([C:17]1[C:18](=[O:34])[C:19]2[C:24]([C:25](=[O:33])[C:26]=1[NH:27][CH2:28][CH2:29][S:30]([CH3:32])=[O:31])=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14](=[O:16])[CH3:15].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:12][N:13]([C:17]1[C:18](=[O:34])[C:19]2[C:24]([C:25](=[O:33])[C:26]=1[NH:27][CH2:28][CH2:29][S:30]([CH3:32])(=[O:9])=[O:31])=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14](=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 22719968HCID 22719968, compound

Product 1

HCID 22719962HCID 22719962, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

80% 3-chloroperbenzoic acid (0.78 g) was added to a solution of N-methyl-N-{3-[2-(methylsulfinyl)ethyl]amino-1,4-dihydro-1,4-dioxo-2-naphthalenyl}acetamide (0.52 g) in dichloromethane (10 ml) and the mixture was stirred at room temperature for 3 hours. Saturated sodium bicarbonate aqueous solution was added to the reaction solution and the mixture was extracted with dichloromethane. The organic layer was washed with water and brine and then dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (elution with chloroform-methanol 50:1 solution) to give N-methyl-N-{3-[2-(methylsulfonyl)ethyl]amino-1,4-dihydro-1,4-dioxo-2-naphthalenyl}acetamide (0.39 g) as an orange amorphous solid.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography (elution with chloroform-methanol 50:1 solution)

Sources & evidence

ORD record
ord-28a921929c1f4fc58b6eae5b4bc53c7a
Source dataset
uspto-grants-2004_05
Patent number
US06734203B2

Reaction notes

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