Triethylamine → N-(4-nitrobenzyl)trifluoroacetoamide

HRID 856657

Reaction equation

HRID 856657 reaction equation
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([O-:4])=[O:3].C(N(CC)CC)C.C([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])(=O)C>C(#N)C>[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][C:24](=[O:23])[C:25]([F:28])([F:27])[F:26])=[CH:11][CH:12]=1)([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1362562,2,2-Trifluoroethyl AcetateHCID 112524674-Nitrobenzylamine hydrochloride

Product 1

HCID 14317262N-(4-nitrobenzyl)trifluoroacetoamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 4-nitrobenzylamine hydrochloride (10.0 g) and triethylamine (22.2 ml) in acetonitrile (100 ml) was added trifluoroethyl acetate (12.6 ml) at room temperature and the mixture was stirred for 24 hours. The solvent was removed under reduced pressure, water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The precipitated crystals were collected by filtration. The crystals were washed with hexane, to give N-(4-nitrobenzyl)trifluoroacetoamide (12.79 g) as colorless crystals.

Workup

  1. customThe solvent was removed under reduced pressure, water
  2. additionwas added to the mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. filtrationThe precipitated crystals were collected by filtration
  8. washThe crystals were washed with hexane

Sources & evidence

ORD record
ord-2b75692cde864675be581d7fbd123640
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Linked notes

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