Water → HCID 15510111, compound

HRID 1530789Notes

Reaction equation

HRID 1530789 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:15](=[O:16])[C:14]([CH3:17])=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:12]=[N:11]1.C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[C:29]#[CH:30].O>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:30][C:29]#[CH:28])=[CH:4][C:3]=1[N:10]1[C:15](=[O:16])[C:14]([CH3:17])=[C:13]([C:18]([F:20])([F:21])[F:19])[CH:12]=[N:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 99490912-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4-methyl-5-(trifluoromethyl)-3(2H)-pyridazinone

Product 1

HCID 15510111HCID 15510111, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Then, 3.2 g of 2-[2-fluoro-4-chloro-5-hydroxyphenyl]-4-methyl-5-trifluoromethylpyridazin-3-one was dissolved in about 50 ml of DMF, to which 2.0 g of potassium carbonate was added at room temperature. Furthermore, 1.3 g of propargyl bromide was added, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was mixed with 100 m of water, and the precipitated crystals were collected by filtration and washed with hexane. The resulting crystals were recrystallized from isopropanol to give 3.4 g of 2-[2-fluoro-4-chloro-5-(2-propynyloxy)phenyl]-4-methyl-5-trifluoromethylpyridazin-3-one (hereinafter referred to as compound A) (m.p., 140.7° C.; decomposition).

Workup

  1. additionwas added at room temperature
  2. filtrationthe precipitated crystals were collected by filtration
  3. washwashed with hexane
  4. customThe resulting crystals were recrystallized from isopropanol

Sources & evidence

ORD record
ord-60af15625dac46c2a7500c31ab19c242
Source dataset
uspto-grants-2001_03
Patent number
US06197727B1

Reaction notes

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