Sodium Methoxide → 3-(Methoxymethyl)-6-[3-(trifluoromethyl)phenyl]-1,2,4-triazolo[4,3-b]pyridazine

HRID 443499Notes

Reaction equation

HRID 443499 reaction equation
Cl[CH2:2][C:3]1[N:7]2[N:8]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1.[CH3:22][O-:23].[Na+]>C(O)C>[CH3:22][O:23][CH2:2][C:3]1[N:7]2[N:8]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 127268623-(Chloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,2,4-triazolo[4,3-b]pyridazine

Product 1

HCID 127268663-(Methoxymethyl)-6-[3-(trifluoromethyl)phenyl]-1,2,4-triazolo[4,3-b]pyridazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.1 g. of 3-(chloromethyl)-6-[3-(trifluoromethyl)phenyl]-1,2,4-triazolo[4,3-b]pyridazine and 0.40 g. of sodium methoxide in 50 ml. of ethanol is refluxed for 24 hours. The solvent is removed under reduced pressure and the residue is dissolved in dichloromethane. The solution is filtered through a column of hydrous magnesium silicate. The eluent is concentrated and hexane added to give 1.4 g. of the product of the Example as crystals, m.p. 149°-150° C. Recrystallization from dichloromethane-hexane gives 0.6 g. of white crystals, m.p. 149°-151° C.

Workup

  1. additionA mixture of 2.1 g
  2. customThe solvent is removed under reduced pressure
  3. dissolutionthe residue is dissolved in dichloromethane
  4. filtrationThe solution is filtered through a column of hydrous magnesium silicate
  5. concentrationThe eluent is concentrated
  6. additionhexane added
  7. customto give 1.4 g
  8. customRecrystallization from dichloromethane-hexane
  9. customgives 0.6 g

Sources & evidence

ORD record
ord-d7995657b7704566a7b21a26888cc4fe
Source dataset
uspto-grants-1981_04
Patent number
US04260755

Reaction notes

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