m-Chloroperbenzoic acid → 2,4-dimethyl-3-chloromethylpyridine-N-oxide

HRID 1693

Reaktionsgleichung

Reaktionsgleichung von HRID 1693
[CH3:1][C:2]1[C:7]([CH2:8][Cl:9])=[C:6]([CH3:10])[CH:5]=[CH:4][N:3]=1.ClC1C=CC=C(C(OO)=[O:19])C=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:7]([CH2:8][Cl:9])=[C:6]([CH3:10])[CH:5]=[CH:4][N+:3]=1[O-:19]

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 196909773-(Chloromethyl)-2,4-dimethylpyridine

Produkt 1

HCID 196909962,4-dimethyl-3-chloromethylpyridine-N-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The 2,4-dimethyl-3-chloromethylpyridine (21.5 g, 138 mmol) was dissolved in CHCl3 (800 mL) and cooled under nitrogen to 0° C. and m-chloroperbenzoic acid (55%, 35 g) was added in small portions. The reaction was stirred for 4 hours. The solution was extracted twice with saturated aqueous sodium bicarbonate (500 mL). The organic phase was dried with MgSO4, filtered and the solvent removed under reduced pressure. The residue was chromatographed on silica gel packed in 98:2 CH2 Cl2 :MeOH and eluted with same. The appropriate fractions were combined and the solvent was removed under reduced pressure the give the desired 2,4-dimethyl-3-chloromethylpyridine-N-oxide.

Aufarbeitung

  1. extractionThe solution was extracted twice with saturated aqueous sodium bicarbonate (500 mL)
  2. dry with materialThe organic phase was dried with MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customThe residue was chromatographed on silica gel
  6. washMeOH and eluted with same
  7. customthe solvent was removed under reduced pressure the

Quellen und Nachweise

ORD-Eintrag
ord-bc2379efbe054eccaf35ae30843004da
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726172

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