Sodium Azide → HCID 57749436, compound

HRID 1162425Notes

Reaction equation

HRID 1162425 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11](Cl)=[O:12])[N:10]=2)[N:7]=1.[N-:14]=[N+:15]=[N-:16].[Na+].C([O-])(O)=O.[Na+]>CC(C)=O>[N:14]([C:11]([C:9]1[N:10]=[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[N:7][N:6]2[CH:8]=1)=[O:12])=[N+:15]=[N-:16]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 577494296-Chloroimidazo[1,2-b]pyridazine-2-carbonyl chloride

Product 1

HCID 57749436HCID 57749436, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 6-chloroimidazo[1,2-b]pyridazine-2-carbonyl chloride from Step 1 (2.2 g, 10 mmol) in acetone (40 mL) was added sodium azide (0.43 g, 6.6 mmol, solution in 1.5 mL H2O). The mixture was stirred at 25° C. for 1 h then poured into aq. NaHCO3. The solid precipitate was collected by careful filtration. The filtercake was not allowed to go dry (solvent-free). The filtercake was washed with benzene (2×50 mL) and then transferred to a 150-mL, round-bottomed flask. To azeotropically remove residual water, the solid was suspended in benzene (75 mL) and then concentrated to one-third its volume. Then once again the material was suspended in benzene (75 mL) and concentrated to near dryness to provide the title compound, which was taken on to the next step without further purification.

Workup

  1. filtrationThe solid precipitate was collected by careful filtration
  2. customto go dry (solvent-free)
  3. washThe filtercake was washed with benzene (2×50 mL)
  4. concentrationconcentrated to one-third its volume
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-986a0a74087a4f8a961d4020fe3e4147
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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