Hydrazinecarboxaldehyde → 6-(3-Thienyl)-1,2,4-triazolo[4,3-b]pyridazine

HRID 443515Notes

Reaction equation

HRID 443515 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)=[CH:6][CH:7]=1.[CH:13]([NH:15][NH2:16])=O>C(O)CCC>[S:10]1[CH:11]=[CH:12][C:8]([C:5]2[CH:6]=[CH:7][C:2]3[N:3]([CH:13]=[N:15][N:16]=3)[N:4]=2)=[CH:9]1

Participants

4

Reactant 2

HCID 12229HydrazinecarboxaldehydeHCID 135734813-Chloro-6-(3-thienyl)pyridazine

Product 1

HCID 234675826-(3-Thienyl)-1,2,4-triazolo[4,3-b]pyridazine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 1.5 g. of 3-chloro-6-(3-thienyl)pyridazine and 0.96 g. of formic acid hydrazide in 50 ml. of n-butyl alcohol is heated at the reflux temperature for 48 hours. The reaction mixture is concentrated free of volatiles and the residue is partitioned between dilute sodium hydroxide and methylene chloride. The organic layer is dried over anhydrous sodium sulfate, filtered and evaporated. The residue is recrystallized from methylene chloride-hexane to give a solid. The solid is recrystallized from acetone-hexane to provide 1.0 g. of the product of the Example as a orange-cream solid, m.p. 189°-192° C.

Workup

  1. additionA mixture of 1.5 g
  2. concentrationThe reaction mixture is concentrated free of volatiles
  3. customthe residue is partitioned between dilute sodium hydroxide and methylene chloride
  4. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is recrystallized from methylene chloride-hexane
  8. customto give a solid
  9. customThe solid is recrystallized from acetone-hexane
  10. customto provide 1.0 g

Sources & evidence

ORD record
ord-0b244675225c4bf0a2dab362cb9a6fc7
Source dataset
uspto-grants-1981_04
Patent number
US04260756

Reaction notes

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