m-Chloroperbenzoic acid → HCID 14627836, compound

HRID 1030238Notes

Reaction equation

HRID 1030238 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([S:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)[CH:8]=[C:7]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:6]=1[OH:21])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:30])C=1>ClCCl>[C:17]([C:7]1[CH:8]=[C:9]([S:11]([C:12]2[S:13][CH:14]=[CH:15][N:16]=2)=[O:30])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:21])([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14627820HCID 14627820, compound

Product 1

HCID 14627836HCID 14627836, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,6-Di-tert-butyl-4-(2-thiazolylthio)phenol (produced in Example 42) (1.60 g) was dissolved in 100 ml of dichloromethane and, with stirring and ice cooling, 1.21 g of 70% m-chloroperbenzoic acid was added, and the mixture was stirred for further 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-ethyl acetate=35:1) gave 1.21 g of the desired product as a colorless solid.

Workup

  1. stirringthe mixture was stirred for further 30 minutes
  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-ethyl acetate=35:1)

Sources & evidence

ORD record
ord-fa7830dc1307451291bbe74716bf1d4d
Source dataset
uspto-grants-1992_04
Patent number
US05104889

Reaction notes

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