Trichloroacetyl chloride → HCID 15472383, compound

HRID 619504Notes

Reaction equation

HRID 619504 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]2[CH:12]=[CH:13][N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1)=[O:5])[CH3:2].[Cl:15][C:16]([Cl:21])([Cl:20])[C:17](Cl)=[O:18]>CN(C)C1C=CN=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:11]2[C:12]([C:17](=[O:18])[C:16]([Cl:21])([Cl:20])[Cl:15])=[CH:13][N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 11127069ethyl imidazo[1,2-a]pyridine-5-carboxylate

Product 1

HCID 15472383HCID 15472383, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of 25.22 g (0.133 mol) of 5-ethoxycarbonylimidazo[1,2-a]pyridine and 48.60 g (0.398 mol) of 4-dimethylaminopyridine was added dropwise 72.33 g (0.398 mol) of trichloroacetyl chloride. The mixture was heated for 63 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-hexane=1:1) to give 33.10 g of the desired compound (77.4%, yellow solid).

Workup

  1. temperatureThe mixture was heated for 63 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-hexane=1:1)

Sources & evidence

ORD record
ord-6c076eded19b4dec93070d043d87fdc1
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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