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

HRID 875499Notes

Reaction equation

HRID 875499 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-a3917778eafa41a0b3d65c16184182e9
Source dataset
uspto-grants-2015_03
Patent number
US08981153B2

Reaction notes

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