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

HRID 1588882Notes

Reaction equation

HRID 1588882 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)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 19.9 grams (0.204 mole) of N-methoxy-N-methylamine hydrochloride in 500 ml of methylene chloride was stirred, and 39.3 grams (0.389 mole) of triethylamine was added. Upon completion of addition, the reaction mixture was stirred for ten minutes, and a solution 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. After this time the reaction mixture was stirred vigorously with 300 ml of water. The aqueous layer was separated from the organic layer and was 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. stirringthe reaction mixture was stirred for ten minutes
  3. additionUpon completion of addition
  4. stirringthe reaction mixture was stirred at ambient temperature for 18 hours
  5. customThe aqueous layer was separated from the organic layer
  6. washwas washed with three portions of methylene chloride
  7. dry with materialthe combination was dried with magnesium sulfate
  8. filtrationThe mixture was filtered
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9dec8a04c35642edbf2095196f1dfa32
Source dataset
uspto-grants-1993_06
Patent number
US05223536

Reaction notes

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