HCID 57977975, compound → HCID 178518924, compound

HRID 1865822Notes

Reaction equation

HRID 1865822 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[C:6]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.[Si]([O:27][K])(C)(C)C>C1COCC1>[Cl:1][C:2]1[N:3]=[N:4][C:5]([OH:27])=[C:6]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 57977975HCID 57977975, compoundHCID 178504318HCID 178504318, compound

Product 1

HCID 178518924HCID 178518924, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a round bottom flask was added 3,6-dichloro-4,5-bis(4-chlorophenyl)pyridazine (1000 mg, 2.710 mmol), THF (20 ml) and TMSOK (869 mg, 6.775 mmol). The reaction was stirred at 80° C. for 8 hrs. After this time, the reaction mixture was concentrated. The residue was diluted with water (15 ml). The pH of the resulting solution was adjusted to 4 using 1N HCl. During addition, a solid precipitated. The solid was collected by filtration to give product 6-chloro-4,5-bis(4-chlorophenyl)pyridazin-3-ol as white solid (760 mg, 80% yield). HPLC retention time (method A) 3.535 min; LCMS (M+H)=351.1.

Workup

  1. concentrationAfter this time, the reaction mixture was concentrated
  2. additionThe residue was diluted with water (15 ml)
  3. additionDuring addition
  4. customa solid precipitated
  5. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-2c196959ccbb44fbb6cb088d7bcb947b
Source dataset
uspto-grants-2009_12
Patent number
US07629342B2

Reaction notes

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