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

HRID 1160759Notes

Reaction equation

HRID 1160759 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-2da751994763486a944bf1e666f8bb92
Source dataset
uspto-grants-2010_10
Patent number
US07816526B2

Reaction notes

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