m-Chloroperbenzoic acid → HCID 18509217, compound

HRID 1356697Notes

Reaction equation

HRID 1356697 reaction equation
[NH2:1][C:2]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:3]=1[N:4]([CH3:15])[S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6].ClC1C=CC=C(C(OO)=[O:29])C=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:20][C:18]1[CH:17]=[CH:16][C:3]([N:4]([CH3:15])[S:5]([C:8]2[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=2)(=[O:7])=[O:6])=[C:2]([N:1]=[O:29])[CH:19]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 18509285HCID 18509285, compound

Product 1

HCID 18509217HCID 18509217, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2′-amino-4′-chloro-N-methyl-p-toluenesulfonanilide (1.50 g (4.83 mmol)) in chloroform (20.0 ml), 70% mCPBA (m-chloro-perbenzoic acid) (2.38 g) was added with stirring at room temperature. After being stirred for 3 days at room temperature, saturated aqueous solution of sodium bicarbonate was added to the reaction mixture and the resulting mixture was extracted with chloroform. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography with ethyl acetate-hexane (1:6) as eluent to give 1.15 g (73%) of the title compound as blue-green crystals.

Workup

  1. stirringAfter being stirred for 3 days at room temperature
  2. extractionthe resulting mixture was extracted with chloroform
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9c0bd8ff7a5b443ca4b067191c36fa51
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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