Water → HCID 178522125, compound

HRID 2199240Notes

Reaction equation

HRID 2199240 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](OCC)=[O:11].C(OCC)(=O)C.O>CN(C)C=O>[F:8][C:9]([F:16])([F:15])[C:10]([N:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][NH:3]1)=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 9794Ethyl trifluoroacetateHCID 104392-Aminopyridine

Product 1

HCID 178522125HCID 178522125, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
57.5 °C

Procedure

In 25 ml of N,N-dimethylformamide, 4.7 g (50 mmol) of 2-aminopyridine was dissolved, and 35.5 g (250 mmol) of ethyl trifluoroacetate was added thereto. After that, the mixture was stirred at 55 to 60° C. for 15 hours, and then 100 ml of ethyl acetate and 100 ml of water were added thereto. The resultant mixture was stirred, and then phase separation was conducted. The ethyl acetate layer was further washed with 100 ml of water and with 100 mL of aqueous sodium chloride, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Thus, 9.05 g of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetamide was obtained (95.6%).

Workup

  1. customphase separation
  2. washThe ethyl acetate layer was further washed with 100 ml of water and with 100 mL of aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-79fd52e4c5694112aa5117e15be4c90b
Source dataset
uspto-grants-2016_06
Patent number
US09357776B2

Reaction notes

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