1,2-Dichloroethane → 5-Acetyl-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl]benzamide

HRID 25026Notes

Reaction equation

HRID 25026 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][C:4]=1[C:5]([OH:7])=O.C1C=CC2N(O)N=NC=2C=1.O.C(Cl)CCl.[F:30][C:31]([F:41])([F:40])[C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH2:37])=[CH:34][CH:33]=1>C(Cl)Cl.CN(C=O)C>[C:12]([C:9]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]([CH:8]=1)[C:5]([NH:37][CH2:36][C:35]1[CH:34]=[CH:33][C:32]([C:31]([F:30])([F:40])[F:41])=[CH:39][CH:38]=1)=[O:7])(=[O:14])[CH3:13]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 768044-(Trifluoromethyl)benzylamineHCID 189545915-Acetyl-2-methoxybenzoic acid

Product 1

HCID 219645355-Acetyl-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl]benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-Methoxy-5-acetylbenzoic acid (Step B, 2.5 g, 12.8 mmol), HOBt.H2O (2.08 g, 15.4 mmol), and EDC (3.70 g, 19.3 mmol) in CH2Cl2 (20 ml) and DMF (5 ml) was added 4-(Trifluoromethyl)benzylamine (2.48 g, 14.1 mmol), and the mixture was stirred for 16 hours at room temperature. The reaction mixture was concentrated under reduced pressure and then redissolved in ethyl acetate. The organic layer was washed with 3% K2CO3, 1 N HCl, and brine, dried over Na2SO4, filtered and concentrated. The purification was done by flash chromatography on silica gel column (chloroform:methanol 95:5) to provide the title compound as white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionredissolved in ethyl acetate
  3. washThe organic layer was washed with 3% K2CO3, 1 N HCl, and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe purification

Sources & evidence

ORD record
ord-6aed3cfb206a4de4961a6b5711e6cae0
Source dataset
uspto-grants-2005_02
Patent number
US06858602B2

Reaction notes

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