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

HRID 2403984Notes

Reaction equation

HRID 2403984 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 156.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-methylethylenediamine (27.0 g, 364.0 mmol) and ethyl trifluoroacetate (96.6 ml, 838.0 mmol) in a mixture of acetonitrile (350 ml) and water (7.8 ml, 436 mmol) was refluxed overnight with stirring. Next the solvents were evaporated in vacuo. Residue was re-evaporated with isopropanol (3×100 ml). Residue was dissolved in dichloromethane (500 ml) and left overnight at room temperature. The formed crystals were filtered, washed with dichloromethane and dried in vacuo to provide compound A (96.8 g, 94%) as white solid powder.

Workup

  1. temperaturewas refluxed overnight
  2. customNext the solvents were evaporated in vacuo
  3. customResidue was re-evaporated with isopropanol (3×100 ml)
  4. dissolutionResidue was dissolved in dichloromethane (500 ml)
  5. filtrationThe formed crystals were filtered
  6. washwashed with dichloromethane
  7. customdried in vacuo

Sources & evidence

ORD record
ord-0a6958cb719a469ab12d2f278dae36c1
Source dataset
uspto-grants-2014_08
Patent number
US08802681B2

Reaction notes

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