m-Chloroperbenzoic acid → HCID 23013797, compound

HRID 2424301Notes

Reaction equation

HRID 2424301 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([O:8][C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:16])=[C:4]([O:17][CH3:18])[CH:3]=1.ClC1C=CC=C(C(OO)=[O:27])C=1>ClCCl>[Cl:1][C:2]1[N+:7]([O-:27])=[N:6][C:5]([O:8][C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:16])=[C:4]([O:17][CH3:18])[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 23013844HCID 23013844, compound

Product 1

HCID 23013797HCID 23013797, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.42 g (12.9 mmol) of 6-chloro-3-(2,6-dimethylphenoxy)-4-methoxypyridazine, dichloromethane (110 mL) and 3.34 g (15.4 mmol) of 80% m-chloroperbenzoic acid were mixed, and the mixture was stirred at room temperature for 16 days. The reaction mixture was poured into ice-cold saturated aqueous sodium sulfite solution, and extracted with dichloromethane. The organic layers were combined, washed successively with a saturated aqueous sodium hydrogen carbonate solution, water and brine, and dried over anhydrous sodium sulfate. The solvent was removed, and the residue was purified by silica gel column chromatography to obtain 2.06 g (7.33 mmol, Yield: 56.8%) of 6-chloro-3-(2,6-dimethylphenoxy)-4-methoxypyridazine 1-oxide.

Workup

  1. additionThe reaction mixture was poured into ice-cold saturated aqueous sodium sulfite solution
  2. extractionextracted with dichloromethane
  3. washwashed successively with a saturated aqueous sodium hydrogen carbonate solution, water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-293f221fc23f4e3cba0db099dff96ecd
Source dataset
uspto-grants-2011_06
Patent number
US07964531B2

Reaction notes

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