Hydrochloric Acid → HCID 19436789, compound

HRID 1735003Notes

Reaction equation

HRID 1735003 reaction equation
[CH3:1][N:2]1[C:6]([OH:7])=[CH:5][C:4]([C:8]([F:11])([F:10])[F:9])=[N:3]1.Cl[C:13]1[N:14]=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1.Cl>C1(C)C=CC=CC=1>[CH3:20][O:19][C:17]1[CH:18]=[C:13]([O:7][C:6]2[N:2]([CH3:1])[N:3]=[C:4]([C:8]([F:9])([F:10])[F:11])[CH:5]=2)[N:14]=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 109756123-Chloro-5-methoxypyridazineHCID 178481859HCID 178481859, compound

Product 1

HCID 19436789HCID 19436789, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol (4.0 g, 0.024 mole), 3-chloro-5-methoxypyridazine (3.5 g, 0.024 mole), and 2,6-1-lutidine (3.0 g, 0.028 mole) were heated to reflux in toluene (75 mL) under N2 and held there for 22.5 h. The mixture was poured into diluted HCl (1%) aqueous solution and extracted 2×100 mL with ethyl acetate. The organic layer was extracted with brine followed by dilute NaOH (1%, 2×100 mL). The organic layer was dried (MgSO4), filtered through silica gel with ethyl acetate and evaporated in vacuo to give 5-methoxy-3-[[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy]-pyridazine (6.25 g, 95% yield) as a light brown solid. This solid was recrystallized from ethyl acetate/cyclohexane.

Workup

  1. extractionextracted 2×100 mL with ethyl acetate
  2. extractionThe organic layer was extracted with brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered through silica gel with ethyl acetate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-764ae4d9ef4648afa69be42cd1773951
Source dataset
uspto-grants-1996_07
Patent number
US05536701

Reaction notes

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