Sodium Sulfite → N-[(Oxiran-2-yl)methyl]-N-(1-phenylethyl)-4-propylbenzene-1-sulfonamide

HRID 358422Notes

Reaction equation

HRID 358422 reaction equation
[CH2:1]([N:4]([CH:17]([CH3:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:33])C=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[O:33]1[CH2:3][CH:2]1[CH2:1][N:4]([CH:17]([CH3:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[CH:10][CH:9]=1)(=[O:6])=[O:7]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 13239924HCID 13239924, compound

Product 1

HCID 187619N-[(Oxiran-2-yl)methyl]-N-(1-phenylethyl)-4-propylbenzene-1-sulfonamideYield 91%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 3.27 g (0.01 mole) of N-allyl-N-α-methylbenzyl-4-propylbenzenesulfonamide in 30 ml of chloroform was admixed with 4.31 g (0.02 mole) of metachloroperbenzoic acid for reaction under reflux for 2 hours. Thereafter, an aqueous sodium sulfite solution was added to decompose the excess of the peroxide. After washing with an aqueous sodium bicarbonate solution and water, the chloroform solution was dried over anhydrous magnesium sulfate, concentrated and purified by the silica gel chromatography to obtain the intended product (Compound No. 14). The yield was 91% and the nD25.0 value was found to be 1.5445. The elemental analysis of the product was effected with the results shown below.

Workup

  1. temperatureunder reflux for 2 hours
  2. washAfter washing with an aqueous sodium bicarbonate solution and water
  3. dry with materialthe chloroform solution was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. custompurified by the silica gel chromatography
  6. customto obtain the intended product (Compound No. 14)

Sources & evidence

ORD record
ord-c49020a3f68d4fc995a6922f4c9cb611
Source dataset
uspto-grants-1984_08
Patent number
US04468245

Reaction notes

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