1,2-Dichloroethane → N-methoxy-N-methyl-2-[3-(trifluoromethyl)phenyl]acetamide

HRID 2219714Notes

Reaction equation

HRID 2219714 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.C(Cl)CCl>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 111,2-DichloroethaneHCID 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 EDC (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-4f7f0720650c44c2ab7e6e003cbf06aa
Source dataset
uspto-grants-2008_08
Patent number
US07414071B2

Reaction notes

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