Sodium Sulfite → HCID 178424396, compound

HRID 1821656Notes

Reaction equation

HRID 1821656 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[C:4]([OH:16])[CH:3]=1.ClC1C=CC=C(C(OO)=[O:25])C=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[N+:7]([O-:25])=[N:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[C:4]([OH:16])[CH:3]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 178424394HCID 178424394, compound

Product 1

HCID 178424396HCID 178424396, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

135 mg (0.572 mmol) of 6-chloro-3-(2-methylphenoxy)-4-pyridazinol (Compound No. 128) obtained in Example 1 and methylene chloride (6 mL) were mixed, 247 mg (purity 80%, 1.14 mmol) of m-chloroperbenzoic acid was added to the mixture and the resulting mixture was refluxed for 16 hours with stirring. The mixture was allowed to stand at room temperature for 2 days, the reaction mixture was poured in a saturated aqueous sodium sulfite solution, and washed with methylene chloride. The aqueous layer was made acidic with hydrochloric acid, extracted with methylene chloride, then washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed, and the obtained residue was purified by silica gel column chromatography (YMC GEL, SIL60, 350/250 mesh, eluted with ethyl acetate) to obtain 32.6 mg (0.129 mmol, Yield: 22.6%) of 6-chloro-3-(2-methylphenoxy)-4-pyridazinol 1-oxide (Compound No. 129).

Workup

  1. additionwere mixed
  2. temperaturethe resulting mixture was refluxed for 16 hours
  3. washwashed with methylene chloride
  4. extractionextracted with methylene chloride
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed
  8. customthe obtained residue was purified by silica gel column chromatography (YMC GEL, SIL60, 350/250 mesh, eluted with ethyl acetate)

Sources & evidence

ORD record
ord-b6fa0de990724b798a52be3019d92960
Source dataset
uspto-grants-2009_10
Patent number
US07608563B2

Reaction notes

Loading…