Water → N-Methyl-3-(trifluoromethyl)benzamide

HRID 389091

Reaction equation

HRID 389091 reaction equation
CN.C1COCC1.[CH2:8]([N:10](CC)CC)C.[F:15][C:16]([F:27])([F:26])[C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20](Cl)=[O:21].O>ClCCl>[CH3:8][NH:10][C:20](=[O:21])[C:19]1[CH:23]=[CH:24][CH:25]=[C:17]([C:16]([F:27])([F:26])[F:15])[CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 66615946Methylamine tetrahydrofuran

Product 1

HCID 1490147N-Methyl-3-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 2M methylamine-THF solution (20 ml) was added to a solution of triethylamine (7 ml) in dichloromethane (70 ml), a solution of 3-(trifluoromethyl)benzoyl chloride (5.0 g) in dichloromethane (30 ml) was added dropwise thereto under ice cooling, followed by stirring at room temperature for 72 hours. The reaction solution was poured into water, followed by extraction with chloroform. The organic layer was washed with saturated aqueous sodium bicarbonate solution and then saturated brine in this order and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The residue was dissolved again in ethyl acetate, washed with 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 resulting solid was washed with diisopropylether, to obtain, as a colorless solid, N-methyl-3-(trifluoromethyl)benzamide (1.34 g).

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  3. dry with materialsaturated brine in this order and dried over anhydrous magnesium sulfate
  4. customthe solvent was then evaporated under reduced pressure
  5. dissolutionThe residue was dissolved again in ethyl acetate
  6. washwashed with saturated aqueous sodium bicarbonate solution
  7. dry with materialsaturated brine in this order, and dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. washThe resulting solid was washed with diisopropylether

Sources & evidence

ORD record
ord-74200f13a85849c9a1e20e868422464d
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Linked notes

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