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

HRID 2374641

Reaction equation

HRID 2374641 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-bfb341000a124dcc8151929a50383393
Source dataset
uspto-grants-2008_12
Patent number
US07462644B2

Linked notes

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