Triethylamine hydrochloride → 6-Chloro-3-phenyl[1,2,4]triazolo[4,3-b]pyridazine

HRID 1383838Notes

Reaction equation

HRID 1383838 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[C:9]([NH:17][NH2:18])(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl.C(N(CC)CC)C>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[N:4]([C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[N:17][N:18]=2)[N:3]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 11955BenzoylhydrazineHCID 673313,6-Dichloropyridazine

Product 1

HCID 9114626-Chloro-3-phenyl[1,2,4]triazolo[4,3-b]pyridazineYield 55.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

3,6-Dichloropyridazine (20 g, 134 mmol) was suspended in xylene (200 ml) with benzoylhydrazine (20.1 g, 1.1 mol eq) and triethylamine hydrochloride (20.3 g, 1.1 mol eq) and the reaction mixture was heated under reflux for 2 hours. The solvent was removed under high vacuum and the residue was purified by chromatography on silica gel using 1% methanol in dichloromethane as eluent to give the required product (17.1 g mp=199° C.). 1H NMR (250 MHz, CDCl3) δ7.16 (1 H, d, J=9.7 Hz), 7.53-7.61 (3 H, m), 8.16 (1 H, d, J=9.7 Hz), 8.44-8.50 (2 H, m); MS (ES+) m/e 231 [MH]+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customThe solvent was removed under high vacuum
  4. customthe residue was purified by chromatography on silica gel using 1% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-bface3e019c54452912727664681f0b6
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

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