3,6-Dichloropyridazine → Benzenamine, 3,?5-?dichloro-?4-?[(6-?chloro-?3-?pyridazinyl)?oxy]?-
Reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.[Cl:9][C:10]1[CH:15]=[C:14]([NH2:16])[CH:13]=[C:12]([Cl:17])[C:11]=1[OH:18]>>[Cl:9][C:10]1[CH:15]=[C:14]([CH:13]=[C:12]([Cl:17])[C:11]=1[O:18][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1)[NH2:16]Participants
Procedure
In one embodiment, the process further comprises providing the compound of Formula (I) by contacting 3,6-dichloropyridazine with 2,6-dichloro-4-aminophenol to form 3,5-dichloro-4-((6-chloropyridazin-3-yl)oxy)aniline, hydrolyzing 3,5-dichloro-4-((6-chloropyridazin-3-yl)oxy)aniline and protecting the amine group of 3,5-dichloro-4-((6-chloropyridazin-3-yl)oxy)aniline either before or after the hydrolysis to form the compound of Formula (I). The contacting of 3,6-dichloropyridazine with 2,6-dichloro-4-aminophenol is performed in a polar aprotic solvent (e.g., dimethylacetamide (DMAC)) in the presence of a base (e.g., Cs2CO3) at a reaction temperature between 60 and 120° C. (e.g., about 65° C.). Further, a purification step may be included. That is, before step (a), the compound of Formula (I) is purified in an acidic solution at a temperature between 80 and 100° C.
Sources & evidence
- ORD record
- ord-dd6fb9942fb7449fae918e9e989db8ab
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266861B2
Reaction notes
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