Water → HCID 53653159, compound

HRID 1075544Notes

Reaction equation

HRID 1075544 reaction equation
[CH3:1][C:2]1[N:6]2[N:7]=[CH:8][CH:9]=[C:10]([CH2:11][CH3:12])[C:5]2=[N:4][N:3]=1.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>C(Cl)(Cl)(Cl)Cl>[Br:13][CH:11]([C:10]1[C:5]2[N:6]([C:2]([CH3:1])=[N:3][N:4]=2)[N:7]=[CH:8][CH:9]=1)[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 53997558HCID 53997558, compound

Product 1

HCID 53653159HCID 53653159, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of crude 3-methyl-8-ethyl-1,2,4-triazolo[4,3-b]pyridazine (0.6 g) was dissolved in anhydrous carbon tetrachloride (40 ml) and N-bromosuccinimide (0.66 g) with a catalytic amount of benzoylperoxide. The total mixture was stirred at room temperature for 45 minutes and then boiled under reflux for 2 hours. The solvent was eliminated at reduced pressure and water (100 ml) was added to the residual oil. The product was extracted with ethyl acetate. The organic layer was washed with 5% aqueous sodium bicarbonate solution, then with water, dried with sodium sulphate, filtered and concentrated to dryness. The residual oil was purified by flash chromatography on silica gel using ethyl acetate as eluent to give 8-(1-bromoethyl)-3-methyl-1,2,4-triazolo[4,3-b]pyridazine as a solid. Yield 0.41 g, m.p. 125-128° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. additionwas added to the residual oil
  3. extractionThe product was extracted with ethyl acetate
  4. washThe organic layer was washed with 5% aqueous sodium bicarbonate solution
  5. dry with materialwith water, dried with sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residual oil was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-6029d920168a42a8990ef26990747797
Source dataset
uspto-grants-1999_05
Patent number
US05905079

Reaction notes

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