Water → HCID 2470061, compound
Reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:13]([Cl:14])=[CH:12][N:11]=[N:10][C:9]=1[OH:15].Cl[CH2:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.O>CS(C)=O.ClCCl>[Cl:7][C:8]1[C:9](=[O:15])[N:10]([CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[N:11]=[CH:12][C:13]=1[Cl:14]Participants
Conditions
- Temperature
- 50 °C
Procedure
9.0 g (65 mmol) of potassium carbonate were added to a solution of 10.0 g (60.61 mmol) of 4,5-dichloro-3-hydroxy-pyridazine in 50 ml dimethylsulphoxide, then 9.42 g (63 mmol) of 1-(chloromethyl)-naphthalene were added and the mixture was stirred for 17 hours at 50° C. The dark solution was cooled and then combined with 300 ml of dist. water, then 300 ml dichloromethane were stirred in, the mixture was suction filtered through Celite, the aqueous phase was separated off and extracted another three times with 50 ml of dichloromethane. The combined organic phases were washed with water, dried over sodium sulphate and evaporated down. The crude product thus obtained was dissolved in 250 ml dichloromethane, the solution was filtered through silica gel and then evaporated down. The residue was triturated with petroleum ether, suction filtered and dried.
Workup
- temperatureThe dark solution was cooled
- filtrationfiltered through Celite
- customthe aqueous phase was separated off
- extractionextracted another three times with 50 ml of dichloromethane
- washThe combined organic phases were washed with water
- dry with materialdried over sodium sulphate
- customevaporated down
Sources & evidence
- ORD record
- ord-ae52026fb9a54e67bd75373be3921540
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109192B2
Reaction notes
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