Water → 2,2,2-trifluoro-N-[2-(methylamino)ethyl]acetamide

HRID 576556Notes

Reaction equation

HRID 576556 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][NH2:5].[F:6][C:7]([F:14])([F:13])[C:8]([O:10]CC)=O.O>C(#N)C>[F:14][C:7]([F:6])([F:13])[C:8]([NH:5][CH2:4][CH2:3][NH:2][CH3:1])=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 8014N-MethylethylenediamineHCID 9794Ethyl trifluoroacetate

Product 1

HCID 107022842,2,2-trifluoro-N-[2-(methylamino)ethyl]acetamideYield 142.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-methylethylenediamine (27.0 g, 364 mmol) and ethyl trifluoroacetate (96.6 mL, 812 mmol) in a mixture of ACN (350 mL) and water (7.8 mL, 436 mmol) was refluxed with stirring overnight. Solvents were evaporated in vacuo. The residue was re-evaporated with i-PrOH (3×100 mL), followed by heat-cool crystallization from DCM (500 mL). Formed crystals were filtered, washed with DCM and dried in vacuo to provide compound A (88.3 g, 85%) as white solid powder.

Workup

  1. temperaturewas refluxed
  2. customSolvents were evaporated in vacuo
  3. customThe residue was re-evaporated with i-PrOH (3×100 mL)
  4. temperatureby heat-cool
  5. customcrystallization from DCM (500 mL)
  6. customFormed crystals
  7. filtrationwere filtered
  8. washwashed with DCM
  9. customdried in vacuo

Sources & evidence

ORD record
ord-ef2cb71fd4f342d3abac933a8fb91d2e
Source dataset
uspto-grants-2015_05
Patent number
US09040032B2

Reaction notes

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