m-Chloroperbenzoic acid → HCID 14627837, compound

HRID 1030239Notes

Reaction equation

HRID 1030239 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([S:11]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[O:12])[CH:8]=[C:7]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=1[OH:22])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:31])C=1>ClCCl>[C:1]([C:5]1[CH:10]=[C:9]([S:11]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)(=[O:31])=[O:12])[CH:8]=[C:7]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=1[OH:22])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14627836HCID 14627836, compound

Product 1

HCID 14627837HCID 14627837, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,6-Di-tert-butyl-4-(2-thiazolylsulfinyl)phenol (produced in Example 57) (0.87 g) was dissolved in 50 ml of dichloromethane and, with ice cooling and stirring, 1.89 g of 70% m-chloroperbenzoic acid was added, and stirring was further continued at room temperature for 30 minutes. The reaction mixture was washed with saturated aqueous sodium bicarbonate solution and then with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated. Purification of the crude product obtained by silica gel column chromatography (chloroform) gave 0.50 g of the desired compound as a colorless solid.

Workup

  1. stirringstirring
  2. washThe reaction mixture was washed with saturated aqueous sodium bicarbonate solution
  3. dry with materialwith saturated aqueous sodium chloride solution, dried over magnesium sulfate
  4. concentrationconcentrated
  5. customPurification of the crude product
  6. customobtained by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-b36673f2cb004d419b3570fd7d84b486
Source dataset
uspto-grants-1992_04
Patent number
US05104889

Reaction notes

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