1-Chloro-2-(diethylamine)ethane hydrochloride → N-methoxy-N-methyl-2-[3-(trifluoromethyl)phenyl]acetamide

HRID 478866Notes

Reaction equation

HRID 478866 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].[F:6][C:7]([F:19])([F:18])[C:8]1[CH:9]=[C:10]([CH2:14][C:15](O)=[O:16])[CH:11]=[CH:12][CH:13]=1.C1C=CC2N(O)N=NC=2C=1.Cl.C(N(CC)CCCl)C>CN(C=O)C.C(Cl)Cl.C(N(CC)CC)C>[CH3:5][O:4][N:3]([CH3:2])[C:15](=[O:16])[CH2:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:7]([F:19])([F:18])[F:6])[CH:9]=1

Participants

8

Reactant 4

HCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 676953-(Trifluoromethyl)benzeneacetic acidHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 22712418N-methoxy-N-methyl-2-[3-(trifluoromethyl)phenyl]acetamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of N,O-dimethylhydroxylamine hydrochloride (1.577 g, 16.2 mmol) in DMF (25 mL) and CH2Cl2 (25 mL) at 0° C. was added triethylamine (2.25 mL). After stirring for 5 minutes, 3-trifluoromethylphenyl acetic acid (3.0 g, 14.7 mmol), HOBT (3.177 g, 23.5 mmol), and DEC (2-diethylaminoethyl chloride hydrochloride, 3.10 g, 16.2 mmol) were added. The reaction mixture was stirred at room temperature for 18 h and was concentrated in vacuo. The residue was diluted with EtOAc and the organic solution was washed consecutively with 1N NaOH (2 times), water, and brine. The organic solution was dried (MgSO4), filtered and concentrated in vacuo. Medium pressure chromatography (20% EtOAc in hexanes to 50% EtOAc in hexanes) provided N-methoxy-N-methyl-2-(3-trifluoromethyl-phenyl)-acetamide.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 h
  2. concentrationwas concentrated in vacuo
  3. additionThe residue was diluted with EtOAc
  4. washthe organic solution was washed consecutively with 1N NaOH (2 times), water, and brine
  5. dry with materialThe organic solution was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b7a016ee2712473c88698a18996d9749
Source dataset
uspto-grants-2003_11
Patent number
US06642266B2

Reaction notes

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