Sodium Carbonate → 3,5-Dichloro-4-chloromethyl-pyridine 1-oxide

HRID 1959544Notes

Reaction equation

HRID 1959544 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:10])[C:7]=1[CH2:8][Cl:9].C([O-])([O-])=[O:12].[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:12])[CH:5]=[C:6]([Cl:10])[C:7]=1[CH2:8][Cl:9]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 226268533,5-Dichloro-4-(chloromethyl)pyridine

Product 1

HCID 670774363,5-Dichloro-4-chloromethyl-pyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3,5-dichloro-4-chloromethyl-pyridine (0.55 g, 2.8 mmol) in DCM (10 mL) 3-methyl-benzenecarboperoxoic acid (2.9 g, 16.8 mmol) was added. After stirring for 50 h at room temperature, saturated aqueous Na2CO3 solution (20 mL) and DCM (40 mL) were added to the reaction mixture. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography over silica gel (elution with EA/hexane 1:2) to give the title compound. MS (m/z): 214.2 [M+H+].

Workup

  1. dry with materialThe organic layer was dried over Na2SO4
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography over silica gel (elution with EA/hexane 1:2)

Sources & evidence

ORD record
ord-1fe4e755d4c64f0eb1e08a3a99443bd1
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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