Triethylamine → N-Methoxy-N-methyl-3-(trifluoromethyl)benzamide

HRID 394469Notes

Reaction equation

HRID 394469 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].Cl.[CH3:15][NH:16][O:17][CH3:18].C(N(CC)CC)C>C(Cl)Cl>[CH3:18][O:17][N:16]([CH3:15])[C:6](=[O:7])[C:5]1[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:13])([F:12])[F:1])[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 14069349N-Methoxy-N-methyl-3-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(Trifluoromethyl)-benzoyl chloride (5 mL, 332 mmol), N,O-dimethyl-hydroxylamine hydrochloride (42 g, 431 mmol) and methylene chloride were combined under argon, then cooled in an ice bath. Triethylamine (108 mL, 775 mmol) was added dropwise with stirring over 0.5 h. The contents of the reaction flask were then warmed to room temperature slowly. After 18 h, the reaction suspension was washed successively with 5% potassium bisulfate, sat. sodium bicarbonate and brine. The organic layer was dried over anhydrous sodium sulfate then concentrated in vacuo to give Compound 1 as an oil: 82 g, (332 mmol, 100%)

Workup

  1. temperaturecooled in an ice bath
  2. waitAfter 18 h
  3. washthe reaction suspension was washed successively with 5% potassium bisulfate, sat. sodium bicarbonate and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-1a6fb97c0edc4d2d8494bab20060f2f2
Source dataset
uspto-grants-2003_08
Patent number
US06602872B1

Reaction notes

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