Water → 6-Chloro-3-(2-methoxy-5-methylphenoxy)pyridazine 1-oxide

HRID 1821667

Reaction equation

HRID 1821667 reaction equation
CC(C)([O-])C.[K+].Cl[C:8]1[N:9]=[N+:10]([O-:15])[C:11]([Cl:14])=[CH:12][CH:13]=1.O.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:20]=1[OH:26]>O1CCOCC1.CS(C)=O>[Cl:14][C:11]1[N+:10]([O-:15])=[N:9][C:8]([O:26][C:20]2[CH:21]=[C:22]([CH3:25])[CH:23]=[CH:24][C:19]=2[O:18][CH3:17])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 145192-Methoxy-5-methylphenolHCID 2609103,6-Dichloropyridazine 1-oxideHCID 23665647Potassium tert-butoxide

Product 1

HCID 229400166-Chloro-3-(2-methoxy-5-methylphenoxy)pyridazine 1-oxideYield 70.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 312751,4-DioxaneSolvent

Procedure

In a mixed solvent of 1,4-dioxane (3 mL) and dimethylsulfoxide (3 mL) was dissolved 167.5 mg (1.21 mmol) of commercially available 2-methoxy-5-methylphenol, and 142.8 mg (1.27 mmol) of potassium tert-butoxide was added to the solution, then 202.9 mg (1.23 mmol) of 3,6-dichloropyridazine 1-oxide was added to the mixture and the resulting mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was successively washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off and the obtained residue was purified by preparative thin-layer chromatography (available from MERCK CO., 1.05744, 3 plates were used, developed by ethyl acetate:hexane=2:1) to obtain 226.5 mg (0.849 mmol, Yield: 70.2%) of 6-chloro-3-(2-methoxy-5-methylphenoxy)pyridazine 1-oxide.

Workup

  1. additionwas added to the solution
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was successively washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe obtained residue was purified by preparative thin-layer chromatography (available from MERCK CO., 1.05744, 3 plates were used, developed by ethyl acetate:hexane=2:1)

Sources & evidence

ORD record
ord-1b8cca4cc3cd466abd35091009dc7e40
Source dataset
uspto-grants-2009_10
Patent number
US07608563B2

Linked notes

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