Triethylamine → 2-Chloro-6-propylimidazo[1,2-b]pyridazine-3-sulfonyl chloride

HRID 1946443Notes

Reaction equation

HRID 1946443 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH3:12])=[N:6][N:5]2[CH:13]=1.[Cl:14][S:15](O)(=[O:17])=[O:16].C(N(CC)CC)C.P(Cl)(Cl)(Cl)=O>ClCCCl.O>[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH3:12])=[N:6][N:5]2[C:13]=1[S:15]([Cl:14])(=[O:17])=[O:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24638Chlorosulfonic acidHCID 24813Phosphorus oxychlorideHCID 230280952-Chloro-6-propylimidazo[1,2-b]pyridazine

Product 1

HCID 230281052-Chloro-6-propylimidazo[1,2-b]pyridazine-3-sulfonyl chloride

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

2-Chloro-6-n-propylimidazo[1,2-b]pyridazine (5.00 g, 25.6 mmol) was dissolved in 1,2-dichloroethane (30.0 ml), and chlorosulfonic acid (3.40 ml, 51.1 mmol) was added to the solution at room temperature. The mixture was heated for 8.5 hours under reflux, and then cooled to room temperature, and triethylamine (7.84 ml, 56.2 mmol) and phosphorus oxychloride (5.24 ml, 56.2 mmol) were added thereto and heated for 4 hours under reflux. Cold water was added to the reaction mixture which was then extracted with chloroform. The extracts were combined, dried over anhydrous magnesium sulfate, filtered and concentrated. The concentrated residues were purified by silica gel column chromatography (ethyl acetate:hexane=3:7) to give the title compound as pale yellow crystals. The yield was 7.40 g (98.4%).

Workup

  1. temperatureThe mixture was heated for 8.5 hours
  2. temperatureunder reflux
  3. temperatureheated for 4 hours
  4. temperatureunder reflux
  5. extractionwas then extracted with chloroform
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe concentrated residues were purified by silica gel column chromatography (ethyl acetate:hexane=3:7)

Sources & evidence

ORD record
ord-b87c22d4acef486a9760aa24b36c5e57
Source dataset
uspto-grants-2013_03
Patent number
US08399381B2

Reaction notes

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