Chloroacetaldehyde → Imidazo(1,2-b)pyridazine, 6-chloro-

HRID 241633Notes

Reaction equation

HRID 241633 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.Cl[CH2:10][CH:11]=O.C(=O)(O)[O-].[Na+]>C(O)CCC>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:10]=[CH:11][N:1]=2)[N:4]=1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 216436-Amino-3-chloropyridazineHCID 516892Sodium Bicarbonate

Product 1

HCID 138828Imidazo(1,2-b)pyridazine, 6-chloro-Yield 70.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

5.0 g (38.6 mmol) of 3-amino-6-chloropyridazine were heated together with 4.7 ml (40 mmol) of chloracetaldehyde (55% strength in water) in 15 ml of n-butanol at 120° C. for a period of 5 days. After the reaction was complete, the reaction mixture was added to saturated sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic phases were then washed with sat. sodium chloride solution and dried over sodium sulfate, and the solvent was removed in vacuo. In the final purification by chromatography on silica gel, 4.17 g (70%) of the desired product were isolated in the form of an amorphous white solid.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic phases were then washed with sat. sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed in vacuo
  5. customIn the final purification by chromatography on silica gel

Sources & evidence

ORD record
ord-e892c5b2079a4e018c4dea246b785ffa
Source dataset
uspto-grants-2014_02
Patent number
US08653076B2

Reaction notes

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