Acetic Acid → N-{[4-(Trifluoromethoxy)phenyl]methyl}acetamide

HRID 1725218

Reaction equation

HRID 1725218 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1.[C:14](O)(=[O:16])[CH3:15].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C.C(OCC)(=O)C>[F:1][C:2]([F:12])([F:13])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH:9][C:14](=[O:16])[CH3:15])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 5718464-(Trifluoromethoxy)benzylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 44542707N-{[4-(Trifluoromethoxy)phenyl]methyl}acetamideYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(trifluoromethoxy)benzylamine (3.46 g, 57.6 mmol) in DMF (75 mL) and acetic acid (10.0 g, 52.3 mmol) at −10° C. were added O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (20.2 g, 62.8 mmol) and N,N-diisopropylethylamine (20.0 mL, 115 mmol) and the reaction mixture was stirred at room temperature overnight. Ethyl acetate (200 mL) was added and the organic phase was washed with water (100 mL), 0.25 M NaOH (100 mL), saturated aqueous NaHCO3 (100 mL), water (100 mL), 0.5 M HCl (100 mL), and water (100 mL), dried over MgSO4, and concentrated in vacuo to afford 11.2 g (92%) of a colourless oil.

Workup

  1. washthe organic phase was washed with water (100 mL), 0.25 M NaOH (100 mL), saturated aqueous NaHCO3 (100 mL), water (100 mL), 0.5 M HCl (100 mL), and water (100 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99f12c5549444f3faedccd5ccca03911
Source dataset
uspto-grants-2009_02
Patent number
US07488844B2

Linked notes

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