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Water → 2-t-butyl-4-chloro-5-[{6-(2,2,3,3-tetrafluoropropyloxy)-3-pyridyl}-methylthio]-3(2H)-pyridazinone

HRID 1904255
Notes
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Reaction equation

HRID 1904255 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([SH:13])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]([F:29])([F:28])[CH:25]([F:27])[F:26])=[N:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([S:13][CH2:15][C:16]2[CH:21]=[N:20][C:19]([O:22][CH2:23][C:24]([F:29])([F:28])[CH:25]([F:27])[F:26])=[CH:18][CH:17]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 134692424-Chloro-2-(1,1-dimethylethyl)-5-mercapto-3(2H)-pyridazinoneHCID 146718285-Chloromethyl-2-(2,2,3,3-tetrafluoropropyloxy)-pyridine

Product 1

HCID 146718292-t-butyl-4-chloro-5-[{6-(2,2,3,3-tetrafluoropropyloxy)-3-pyridyl}-methylthio]-3(2H)-pyridazinoneYield 90.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 40 ml of acetonitrile were dissolved 2.2 g of 2-t-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone and 2.7 g of 5-chloromethyl-2-(2,2,3,3-tetrafluoropropyloxy)-pyridine, and thereto was added 1.5 g of potassium carbonate. The reaction mixture was stirred overnight at room temperature, poured into water and extracted with benzene. The organic layer was washed with a 5% aqueous solution of sodium hydroxide and then with water, and dried over anhydrous sodium sulfate. Solvent was distilled off under reduced pressure and the resulting crystals were washed with n-hexane to obtain 4.0 g of 2-t-butyl-4-chloro-5-[{6-(2,2,3,3-tetrafluoropropyloxy)-3-pyridyl}-methylthio]-3(2H)-pyridazinone, m.p. 113.0°~114.0° C.

Workup

  1. extractionextracted with benzene
  2. washThe organic layer was washed with a 5% aqueous solution of sodium hydroxide
  3. dry with materialwith water, and dried over anhydrous sodium sulfate
  4. distillationSolvent was distilled off under reduced pressure
  5. washthe resulting crystals were washed with n-hexane

Sources & evidence

ORD record
ord-ec069042ebfe4ee58791184e9f2db47b
Source dataset
uspto-grants-1989_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04837217

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes