3-(Trifluoromethoxy)aniline → HCID 68664707, compound

HRID 452665Notes

Reaction equation

HRID 452665 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6].[F:15][C:16]([F:26])([F:25])[O:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21].C(N(CC)C(C)C)(C)C>CS(C)=O.C(OCC)(=O)C>[N+:12]([C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[NH:21][C:20]1[CH:22]=[CH:23][CH:24]=[C:18]([O:17][C:16]([F:15])([F:25])[F:26])[CH:19]=1)([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 737533-(Trifluoromethoxy)anilineHCID 81531DiisopropylethylamineHCID 592761Methyl 3-fluoro-4-nitrobenzoate

Product 1

HCID 68664707HCID 68664707, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 3-fluoro-4-nitrobenzoate (4.66 g, 23.4 mmol), 3-trifluoromethoxyaniline (4.98 g, 28.1 mmol) and N,N-diisopropylethylamine (4.84 mL, 28.1 mmol) in dimethyl sulfoxide (30 mL) was stirred at 120° C. overnight. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane/tetrahydrofuran to give the title compound (2.90 g, yield 35%) as red crystals.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from hexane/tetrahydrofuran

Sources & evidence

ORD record
ord-f36263c3e7ed4b19a7f44a2510045dd1
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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