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

HRID 591137Notes

Reaction equation

HRID 591137 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]acetamide

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 stiffing 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 AA (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
  10. customto provide compound AA (88.3 g, 85%) as white solid powder

Sources & evidence

ORD record
ord-2a7262f6cb7a4a7da8711f6bd247e1d9
Source dataset
uspto-grants-2016_01
Patent number
US09238020B2

Reaction notes

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