Triethylamine → 4-fluoro-N-methyl-2-(trifluoromethyl)benzamide

HRID 389089

Reaction equation

HRID 389089 reaction equation
C(Cl)(=O)C(Cl)=O.[F:7][C:8]1[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[C:10]([C:17]([F:20])([F:19])[F:18])[CH:9]=1.CN.C1COCC1.[CH2:28]([N:30](CC)CC)C>CN(C=O)C.ClCCl>[F:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH:30][CH3:28])=[O:13])=[C:10]([C:17]([F:20])([F:19])[F:18])[CH:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 6882554-Fluoro-2-(trifluoromethyl)benzoic acidHCID 66615946Methylamine tetrahydrofuran

Product 1

HCID 220950754-fluoro-N-methyl-2-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

DMF (3 drops) and oxalyl chloride (2.55 ml) were added to a mixture of 4-fluoro-2-(trifluoromethyl)benzoic acid (5.50 g) and dichloromethane (50 ml), followed by stirring at room temperature for 3 hours. The reaction solution was added dropwise to a 2M methylamine-THF solution (17.3 ml) and a solution of triethylamine (5.55 ml) in dichloromethane (50 ml) under ice cooling, followed by stirring for 30 minutes and concentration under reduced pressure, addition of water and extraction with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium bicarbonate solution and then saturated brine in this order, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with diisopropylether to obtain 4-fluoro-N-methyl-2-(trifluoromethyl)benzamide (4.37 g) as a white solid.

Workup

  1. stirringby stirring for 30 minutes
  2. concentrationconcentration
  3. additionunder reduced pressure, addition of water and extraction with ethyl acetate
  4. washThe organic layer was washed with water, saturated aqueous sodium bicarbonate solution
  5. dry with materialsaturated brine in this order, and dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. washThe residue was washed with diisopropylether

Sources & evidence

ORD record
ord-d0fb158523c248fca59354d4fe3383c2
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Linked notes

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