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

HRID 1763581Notes

Reaction equation

HRID 1763581 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:12][CH:13]=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:9]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:12][CH:13]=3)[CH:6]=[CH:7][C:2]2=[N:22][N:21]=1

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 124495523-Chloro-6-[3-(trifluoromethyl)phenyl]pyridazine

Product 1

HCID 1079503-Methyl-6-[3-(trifluoromethyl)phenyl]-1,2,4-triazolo[4,3-b]pyridazine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A 6.0 g. portion of 3-chloro-6-(α ,α ,α-trifluoro-m-tolyl)pyridazine (prepared as in Example 11), 3.44 g. of acetylhydrazine and 75 ml. of n-butyl alcohol is refluxed for 48 hours. The solvent is removed under vacuum and the residue dissolved in ethyl alcohol and treated with activated carbon. The filtrate is concentrated, chilled and filtered to give an orange solid. Recrystallization from methyl alcohol affords the product of the example as crystals, m.p. 193°-194° C.

Workup

  1. customThe solvent is removed under vacuum
  2. dissolutionthe residue dissolved in ethyl alcohol
  3. additiontreated with activated carbon
  4. concentrationThe filtrate is concentrated
  5. temperaturechilled
  6. filtrationfiltered
  7. customto give an orange solid
  8. customRecrystallization from methyl alcohol
  9. customaffords the product of the example as crystals, m.p. 193°-194° C.

Sources & evidence

ORD record
ord-c99db01b8b6a4f78959d0f16e6469a0f
Source dataset
uspto-grants-1978_09
Patent number
US04112095

Reaction notes

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