Allylamine → N-Allyl-2,2,2-trifluoroacetamide

HRID 74327Notes

Reaction equation

HRID 74327 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.[CH2:10]([NH2:13])[CH:11]=[CH2:12]>C1COCC1>[CH2:10]([NH:13][C:3](=[O:5])[C:2]([F:1])([F:8])[F:9])[CH:11]=[CH2:12]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 9794Ethyl trifluoroacetate

Product 1

HCID 558569N-Allyl-2,2,2-trifluoroacetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold solution of ethyl trifluoroacetate (15 mL, 142.2 mmol) in THF (40 mL) was added allylamine (12 mL, 57.1 mmol). The reaction was allowed to warm to room temperature then stirred for 55 min. After the mixture was concentrated under reduced pressure, the residue was dried under vacuum to give acetamide 30. Yield (18.79 g, 98%): 1H NMR (400 MHz, CDCl3) δ 6.46 (br s, 1H), 5.79-5.89 (m, 1H), 5.23-5.29 (m, 2H), 3.98 (t, J=5.6 Hz, 2H).

Workup

  1. concentrationAfter the mixture was concentrated under reduced pressure
  2. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-f8ed64d3995241ea849962f7ca1b4596
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Reaction notes

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