Ethyl trifluoroacetate → N-[1-[1-(6-Chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoroacetamide

HRID 2199247Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[F:8][C:9]([F:16])([F:15])[C:10]([O:12]CC)=O.C(=O)([O-])[O-].[K+].[K+].[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30]Cl)=[CH:26][N:25]=1>CN(C)C=O.C1(C)C=CC=CC=1.O.CO>[Cl:23][C:24]1[N:25]=[CH:26][C:27]([CH2:30][N:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]2=[N:1][C:10](=[O:12])[C:9]([F:8])([F:15])[F:16])=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 62.5 °C

Procedure

In a mixture solvent of 30 mL of dimethylformamide and 20 ml of toluene, 9.4 g (0.1 mol) of 2-aminopyridine was dissolved, and 28.4 g (0.2 mol) of ethyl trifluoroacetate was added thereto, followed by stirring at 60 to 65° C. for 8 hours. To the reaction liquid, 16.6 g (0.12 mol) of potassium carbonate powder and 16.2 g (0.1 mol) of 2-chloro-5-chloromethylpyridine were added, followed by stirring at 60 to 65° C. for 15 hours. To the reaction liquid, 15 mL of methanol was added, and then the reaction liquid was added to 120 mL of hot water of 50° C. After being cooled to room temperature, the mixture was stirred for 2 hours. The crystals were filtered, and washed with 50 mL of water and 100 mL of toluene. The obtained crystals were dried under reduced pressure at 45° C. Thus, 25.6 g of the target compound was obtained (Percentage Yield: 81.2%).

Workup

additionwere added
stirringby stirring at 60 to 65° C. for 15 hours
additionwas added
customthe reaction liquid
temperatureAfter being cooled to room temperature
stirringthe mixture was stirred for 2 hours
filtrationThe crystals were filtered
washwashed with 50 mL of water and 100 mL of toluene
customThe obtained crystals were dried under reduced pressure at 45° C

Sources & evidence

ORD record: ord-27fcaa1e47124c9b9c0e1d7f8961874f
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09357776B2

Reaction notes

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