Acetohydrazide → 3-Methyl-6-[4-(trifluoromethyl)phenyl]-1,2,4-triazolo[4,3-b]pyridazine

HRID 1763592Notes

Reaction equation

HRID 1763592 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.[C:18]([NH:21][NH2:22])(=O)[CH3:19]>C(O)CCC>[CH3:19][C:18]1[N:3]2[N:4]=[C:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=3)[CH:6]=[CH:7][C:2]2=[N:22][N:21]=1

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 12449554Pyridazine, 3-chloro-6-[4-(trifluoromethyl)phenyl]-

Product 1

HCID 103788173-Methyl-6-[4-(trifluoromethyl)phenyl]-1,2,4-triazolo[4,3-b]pyridazine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 4.50 g. of 3-chloro-6-(α,α,α-trifluoro-p-tolyl)pyridazine, 2.58 g. of acethydrazide and 100 ml. of n-butanol is heated at reflux temperature for 3 days. The solvent is removed and the resin dissolved in methylene chloride, passed through magnesol and the solid from the filtrate recrystallized from methylene chloride/hexane to afford the product as tan crystals, m.p. 199°-201° C.

Workup

  1. additionA mixture of 4.50 g
  2. temperatureat reflux temperature for 3 days
  3. customThe solvent is removed
  4. dissolutionthe resin dissolved in methylene chloride
  5. customthe solid from the filtrate recrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-b1d6041999944d96bcb249b10de4a732
Source dataset
uspto-grants-1978_09
Patent number
US04112095

Reaction notes

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