m-Chloroperbenzoic acid → HCID 178440664, compound

HRID 980333Notes

Reaction equation

HRID 980333 reaction equation
C(S[C:9]1[NH:10][CH:11]=[C:12]([C:14]2[CH:19]=[C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:17]([OH:24])=[C:16]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:15]=2)[N:13]=1)C1C=CC=CC=1.ClC1C=CC=C(C(OO)=O)C=1>C(Cl)(Cl)Cl>[C:25]([C:16]1[CH:15]=[C:14]([C:12]2[N:13]=[CH:9][NH:10][CH:11]=2)[CH:19]=[C:18]([C:20]([CH3:21])([CH3:22])[CH3:23])[C:17]=1[OH:24])([CH3:26])([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178440665HCID 178440665, compound

Product 1

HCID 178440664HCID 178440664, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 10 ml of chloroform was dissolved 0.8 g of 2-benzylthio-4-(3,5-di-tert-butyl-4-hydroxyphenyl)imidazole and then 0.35 g of m-chloroperbenzoic acid was added to the solution at room temperature. After the reaction was over, the reaction mixture was washed with a diluted aqueous alkali solution, dried, and concentrated under reduced pressure. The residue formed was subjected to silica gel chromatography and eluted with chloroform. The fraction thus obtained was concentrated udner reduced pressure and the residue was recrystallized from cyclohexane to provide 0.3 g of 2-benzylsulfinyl)-4-(3,5-di-tert-butyl-4-hydroxyphenyl)imidazole.

Workup

  1. washwas washed with a diluted aqueous alkali solution
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue formed
  5. washeluted with chloroform
  6. customThe fraction thus obtained
  7. concentrationwas concentrated udner reduced pressure
  8. customthe residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-8dd5d512f8084da4bf658687e64baffd
Source dataset
uspto-grants-1987_01
Patent number
US04636516

Reaction notes

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