2,2,2-Trifluoroethylamine hydrochloride → Ethanimidic acid, N-(2,2,2-trifluoroethyl)-, ethyl ester

HRID 1188733Notes

Reaction equation

HRID 1188733 reaction equation
Cl.[C:2](=[NH:7])([O:4][CH2:5][CH3:6])[CH3:3].Cl.[F:9][C:10]([F:14])([F:13])[CH2:11]N.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.O>[CH2:5]([O:4][C:2](=[N:7][CH2:11][C:10]([F:14])([F:13])[F:9])[CH3:3])[CH3:6]

Participants

6

Reactant 3

HCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 11430Potassium CarbonateHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)

Product 1

HCID 86618848Ethanimidic acid, N-(2,2,2-trifluoroethyl)-, ethyl esterYield 87.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl acetimidate hydrochloride (1.23 g, 9.95 mmol) and 2,2,2-trifluoroethylamine hydrochloride (1.35 g, 9.95 mmol) were dissolved in CH2Cl2 (32 mL)/H2O (3.2 mL). K2CO3 (0.69 g, 4.98 mmol) was added and stirred for 30 minutes. The two layers were separated. The aqueous layer was extracted with CH2Cl2 (2×10 mL). The combined organic layer was dried with Na2SO4 and concentrated to give 1.48 g of N-(2,2,2-Trifluoro-ethyl)-acetimidic acid ethyl ester as a light yellow liquid in 87% yield.

Workup

  1. customThe two layers were separated
  2. extractionThe aqueous layer was extracted with CH2Cl2 (2×10 mL)
  3. dry with materialThe combined organic layer was dried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e235451692cf4bf2a77136ae0bdd9e18
Source dataset
uspto-grants-2014_03
Patent number
US08674088B2

Reaction notes

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