m-Chloroperbenzoic acid → HCID 67937709, compound

HRID 1193980Notes

Reaction equation

HRID 1193980 reaction equation
[CH3:1][C:2]1([CH3:19])[O:11][C:10]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[C@@H:4]([N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])[C@@H:3]1[OH:18].ClC1C=CC=C(C(OO)=[O:28])C=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:19])[O:11][C:10]2[CH:9]=[CH:8][N+:7]([O-:28])=[CH:6][C:5]=2[C@@H:4]([N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])[C@@H:3]1[OH:18]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14743463HCID 14743463, compound

Product 1

HCID 67937709HCID 67937709, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The compound of example 1 (102mgm) and m-chloroperbenzoic acid (134mgm) were heated under reflux in chloroform (10 mL) for 2hr. The reaction mixture was cooled and evaporated and the resulting gum was chromatographed (chromatotron; chloroform ->10% methanol-chloroform in a gradient elution), and chromatographically homogenous fractions were combined and recrystallised from ethyl acetate-methanol to give the N-oxide of (E2) as a solid (54mgm) of m.p. 284°-285° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated
  3. customthe resulting gum was chromatographed (chromatotron
  4. washchloroform ->10% methanol-chloroform in a gradient elution), and chromatographically homogenous fractions
  5. customrecrystallised from ethyl acetate-methanol

Sources & evidence

ORD record
ord-f3fbec4add7c43ffae8525355ab7f26d
Source dataset
uspto-grants-1989_03
Patent number
US04812459

Reaction notes

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