Sodium Thiosulfate → 6-Chloro-3-iodo-2-phenylimidazo[1,2-b]pyridazine

HRID 1803900Notes

Reaction equation

HRID 1803900 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[N:7]=1.[I:17]Cl.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([I:17])=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[N:7]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 24640Iodine chlorideHCID 137233Imidazo(1,2-b)pyridazine, 6-chloro-2-phenyl-

Product 1

HCID 248624716-Chloro-3-iodo-2-phenylimidazo[1,2-b]pyridazineYield 92.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution, cooled to 0° C., of 10.4 g (45.4 mmol) of 6-chloro-2-phenylimidazo[1,2-b]pyridazine (CAS No.: 1844-53-7) in 500 mL of chloroform is rapidly added dropwise a solution of 11.1 g (68.1 mmol) of iodine monochloride in 100 mL of chloroform. After cooling to room temperature and stirring for 1 hour, the mixture is treated with aqueous 5% sodium thiosulfate solution. The product is extracted with dichloromethane and the organic phase is dried over sodium sulfate and concentrated under reduced pressure. The residue is triturated in 150 ml of acetonitrile containing a few mL of isopropyl alcohol and the solid is isolated after filtration. 15 g of a yellow powder are isolated after drying under vacuum.

Workup

  1. extractionThe product is extracted with dichloromethane
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is triturated in 150 ml of acetonitrile containing a few mL of isopropyl alcohol
  5. customthe solid is isolated
  6. filtrationafter filtration

Sources & evidence

ORD record
ord-501a285d2d334149a20bdc920b7ba632
Source dataset
uspto-grants-2013_01
Patent number
US08354405B2

Reaction notes

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