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

HRID 882392Notes

Reaction equation

HRID 882392 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-cb8a102802c94316995ffa2d022fdd0f
Source dataset
uspto-grants-2015_03
Patent number
US08993807B2

Reaction notes

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