Water → Bis(2,2,2-trichloroethyl) imidazo[1,2-b]pyridazin-6-ylimidodicarbonate

HRID 2263156Notes

Reaction equation

HRID 2263156 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][C:6]([NH2:10])=[N:5]2.Cl[C:12]([O:14][CH2:15][C:16]([Cl:19])([Cl:18])[Cl:17])=[O:13].[OH2:20]>CN(C)C1C=CN=CC=1.O1CCCC1>[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][C:6]([N:10]([C:12]([O:14][CH2:15][C:16]([Cl:19])([Cl:18])[Cl:17])=[O:20])[C:12]([O:14][CH2:15][C:16]([Cl:19])([Cl:18])[Cl:17])=[O:13])=[N:5]2

Participants

6

Reactant 3

HCID 962WaterHCID 870632,2,2-Trichloroethyl chloroformateHCID 10534704Imidazo[1,2-b]pyridazin-6-amine

Product 1

HCID 86625504Bis(2,2,2-trichloroethyl) imidazo[1,2-b]pyridazin-6-ylimidodicarbonateYield 53.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of imidazo[1,2-b]pyridazine-6-amine (1.00 g, 7.45 mmol) and 4-dimethylaminopyridine (2.73 g, 22.4 mmol) in tetrahydrofuran (75 ml) was added 2,2,2-trichloroethyl chloroformate (3.09 ml, 22.4 mmol) with ice-cooling, and the mixture was stirred at 60° C. for 15 hours. Water was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Hexane was added to the residue, and a solid was collected by filtration to give 1.92 g (53.1%) of the desired product.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionHexane was added to the residue
  7. filtrationa solid was collected by filtration

Sources & evidence

ORD record
ord-0d5d21b65dc84dccb42d06375bdcdadd
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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