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

HRID 443514Notes

Reaction equation

HRID 443514 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:6][CH:7]=1.[CH:13]([NH:15][NH2:16])=O>C(O)CCC>[S:9]1[CH:10]=[CH:11][CH:12]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:13]=[N:15][N:16]=2)[N:4]=1

Participants

4

Reactant 2

HCID 12229HydrazinecarboxaldehydeHCID 64047013-Chloro-6-(thiophen-2-yl)pyridazine

Product 1

HCID 142879766-(2-Thienyl)-1,2,4-triazolo[4,3-b]pyridazine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 1.0 g. of 3-chloro-6-(2-thienyl)pyridazine and 0.6 g. of formic acid hydrazide in 50 ml. of n-butyl alcohol is heated at the reflux temperature for 18 hours. The volatiles are removed and the residue is partitioned between dilute aqueous 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 afford a tan solid. The solid is recrystallized from acetone:hexane to give 0.5 g. of the desired product as cream colored crystals, m.p. 155°-159° C.

Workup

  1. additionA mixture of 1.0 g
  2. customThe volatiles are removed
  3. customthe residue is partitioned between dilute aqueous 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
  8. customhexane to afford a tan solid
  9. customThe solid is recrystallized from acetone
  10. customhexane to give 0.5 g

Sources & evidence

ORD record
ord-42c1714a4b82460d998ac35c57546625
Source dataset
uspto-grants-1981_04
Patent number
US04260756

Reaction notes

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