m-Chloroperbenzoic acid → HCID 14229238, compound

HRID 1073725Notes

Reaction equation

HRID 1073725 reaction equation
[CH3:1][N:2]([CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH2:15])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4].ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)(Cl)Cl>[CH3:1][N:2]([CH2:13][C:14]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:30][CH2:15]1)[S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14229138HCID 14229138, compound

Product 1

HCID 14229238HCID 14229238, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 9.8 g of N-methyl-N-(2-phenyl-2-propenyl)-p-toluenesulfonamide, 9.63 g of m-chloroperbenzoic acid and 280 ml of chloroform were stirred at 60° C. for 3 hours. After cooling, the reaction mixture was washed subsequently with 10% aqueous sodium bisulfite and water, dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by silica gel column chromatography (developing solvent:ethyl acetate -n-hexane) to obtain 7.7 g of the titled compound.

Workup

  1. temperatureAfter cooling
  2. washthe reaction mixture was washed subsequently with 10% aqueous sodium bisulfite and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by silica gel column chromatography (developing solvent:ethyl acetate -n-hexane)

Sources & evidence

ORD record
ord-be13ee35283946cba0fcc4e6557157c7
Source dataset
uspto-grants-1990_11
Patent number
US04971620

Reaction notes

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