Trichloroacetyl chloride → HCID 11152275, compound

HRID 619505Notes

Reaction equation

HRID 619505 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]2[CH:12]=[C:13]([CH3:15])[N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1)=[O:5])[CH3:2].[Cl:16][C:17]([Cl:22])([Cl:21])[C:18](Cl)=[O:19]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:11]2[C:12]([C:18](=[O:19])[C:17]([Cl:22])([Cl:21])[Cl:16])=[C:13]([CH3:15])[N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 11148398HCID 11148398, compound

Product 1

HCID 11152275HCID 11152275, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 8.03 g (39.3 mmol) of 5-ethoxycarbonyl-2-methylimidazo[1,2-a]pyridine and 14.41 g (118 mmol) of 4-dimethylaminopyridine in 80 ml of chloroform was added dropwise 21.45 g (118 mmol) of trichloroacetyl chloride. The mixture was heated for 15 hours under reflux. After cooling, the reaction mixture was washed with an aqueous solution of sodium hydrogencarbonate, drid over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent: ethyl acetate/n-hexane=2:1) to give 8.29 g of the desired compound (60.3%, pale yellow solid).

Workup

  1. temperatureThe mixture was heated for 15 hours
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with an aqueous solution of sodium hydrogencarbonate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent: ethyl acetate/n-hexane=2:1)

Sources & evidence

ORD record
ord-648315f49a7b466588c74a13821554e6
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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