HCID 22940135, compound → HCID 22940131, compound
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1[O:9][C:10]1[C:15]([CH:16]([CH3:18])[CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:19].[Cl:20][C:21]1[N:22]=[N:23][C:24]([O:28][C:29]2[C:34]([CH:35]([CH3:37])[CH3:36])=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:38])=[CH:25][C:26]=1Cl>>[Cl:8][C:6]1[N:5]=[N:4][C:3]([O:9][C:10]2[C:15]([CH:16]([CH3:18])[CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:19])=[C:2]([O:28][CH3:24])[CH:7]=1.[Cl:20][C:21]1[N:22]=[N:23][C:24]([O:28][C:29]2[C:34]([CH:35]([CH3:37])[CH3:36])=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:38])=[CH:25][C:26]=1[O:9][CH3:3]Participants
Procedure
To methanol (10 mL) was added 0.080 g (3.5 mmol) of sodium, and the mixture was stirred at room temperature for 30 minutes. To the mixture was added 0.830 g (2.61 mmol) of 4,6-dichloro-3-(2-chloro-6-isopropylphenoxy)pyridazine obtained in (6), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice-cold water, and extracted with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, and the solvent was removed. The obtained residue was purified by silica gel column chromatography (hexane: ethyl acetate=10:1), washed with hexane and crystallized to obtain 0.720 g (2.30 mmol, Yield: 88.1%) of 6-chloro-3-(2-chloro-6-isopropylphenoxy)-4-methoxypyridazine. On the other hand, 1.78 g (5.60 mmol) of the mixture of 4,6-dichloro-3-(2-chloro-6-isopropylphenoxy)pyridazine and 3,4-dichloro-6-(2-chloro-6-isopropylphenoxy)pyridazine was reacted in the same manner as mentioned above to obtain 1.25 g (3.99 mmol, Yield: 71.3%) of 6-chloro-3-(2-chloro-6-isopropylphenoxy)-4-methoxypyridazine and 0.300 g (0.958 mmol, Yield: 17.1%) of 3-chloro-6-(2-chloro-6-isopropylphenoxy)-4-methoxypyridazine.
Sources & evidence
- ORD record
- ord-952d07dfa314487eb149f84834d08e8b
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07608563B2
Reaction notes
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