m-Chloroperbenzoic acid → 2,4-Dichloro-3,6-dimethylpyridine 1-oxide

HRID 968031Notes

Reaction equation

HRID 968031 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([Cl:9])[CH:5]=[C:4]([CH3:10])[N:3]=1.ClC1C=CC=C(C(OO)=[O:19])C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([Cl:9])[CH:5]=[C:4]([CH3:10])[N+:3]=1[O-:19]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 110843982,4-Dichloro-3,6-dimethylpyridine

Product 1

HCID 219122022,4-Dichloro-3,6-dimethylpyridine 1-oxideYield 76.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2,4-dichloro-3,6-dimethyl-pyridine (790 mg, 4.49 mmol) and 50% m-chloro-perbenzoic acid (1.544 g, 4.49 mmol) in 10 ml of chloroform was stirred at room temperature for 20 hours. The mixture was quenched with water, washed with saturated sodium thiosulfate and saturated sodium carbonate, brine and extracted with chloroform. The organic layer was dried and concentrated to give 954 mg of crude material. The material was purified through silica gel to give 662 mg of the title compound as a white crystals, mp 131-132° C. 1H NMR (CDCl3) δ 7.22 (s, 1H), 2.51 (s, 3H), 2.47 (s, 3H) ppm.

Workup

  1. customThe mixture was quenched with water
  2. washwashed with saturated sodium thiosulfate and saturated sodium carbonate, brine
  3. extractionextracted with chloroform
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customto give 954 mg of crude material
  7. customThe material was purified through silica gel

Sources & evidence

ORD record
ord-032444b1fbe0455695a20821715e07e8
Source dataset
uspto-grants-2005_10
Patent number
US06956047B1

Reaction notes

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