Water → N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide

HRID 1383231Notes

Reaction equation

HRID 1383231 reaction equation
Cl.[CH3:2][O:3][NH:4][CH3:5].C(N(CC)CC)C.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1.O>C(Cl)Cl>[CH3:2][O:3][N:4]([CH3:5])[C:19](=[O:20])[C:18]1[CH:22]=[CH:23][C:15]([C:14]([F:25])([F:24])[F:13])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 14069348N-Methoxy-N-methyl-4-(trifluoromethyl)benzamideYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 19.9 grams (0.204 mole) of N-methoxy-N-methylamine hydrochloride in 500 mL of methylene chloride was added 39.3 grams (0.388 mole) of triethylamine. Upon completion of addition, the reaction mixture was stirred for ten minutes, and a solution of 38.4 grams (0.185 mole) of 4-trifluoromethylbenzoyl chloride in 25 mL of methylene chloride was added dropwise. Upon completion of addition, the reaction mixture was stirred at ambient temperature for 18 hours. The reaction mixture was then stirred vigorously with 300 mL of water. The aqueous layer was separated from the organic layer and washed with three portions of methylene chloride. The washes were combined with the organic layer, and the combination was dried with magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure, yielding 42.5 grams of N-methoxy-N-methyl-4-trifluoromethylbenzamide as an oil. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. additionUpon completion of addition
  3. stirringthe reaction mixture was stirred at ambient temperature for 18 hours
  4. customThe aqueous layer was separated from the organic layer
  5. washwashed with three portions of methylene chloride
  6. dry with materialthe combination was dried with magnesium sulfate
  7. filtrationThe mixture was filtered
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ade1b51caa6b467c856872ddd48c8f5c
Source dataset
uspto-grants-1989_02
Patent number
US04808762

Reaction notes

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