Trichloroacetyl chloride → HCID 21190241, compound

HRID 1068819Notes

Reaction equation

HRID 1068819 reaction equation
[Cl:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[Cl:11][C:12]([Cl:17])([Cl:16])[C:13](Cl)=[O:14]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:7]2[C:8]([C:13](=[O:14])[C:12]([Cl:17])([Cl:16])[Cl:11])=[CH:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 109537225-Chloroimidazo[1,2-A]pyridine

Product 1

HCID 21190241HCID 21190241, compoundYield 8.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 45.77 g (0.30 mol) of 5-chloroimidazo[1,2-a]pyridine and 120.9 g (0.99 mol) of 4-dimethylaminopyridine in 500 ml of chloroform was added dropwise 163.5 g (0.90 mol) of trichloroacetyl chloride. The mixture was heated for 43 hours under reflux. After cooling, the reaction mixture was washed with an aqueous solution of sodium hydrogencarbonate, dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent: ethyl acetate/n-hexan=1:1) to give 7.41 g of the desired compound (8.3%, pale brown solid).

Workup

  1. temperatureThe mixture was heated for 43 hours
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with an aqueous solution of sodium hydrogencarbonate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by column chromatography (eluent: ethyl acetate/n-hexan=1:1)

Sources & evidence

ORD record
ord-baa089a30e13422ca00dd598a50af42f
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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