Cesium carbonate → N-[3-(4-amino-2-nitrophenoxy)phenyl]-2,2,2-trifluoroacetamide

HRID 455220Notes

Reaction equation

HRID 455220 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=1)=[O:4].F[C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[NH2:20][C:19]1[CH:21]=[CH:22][C:16]([O:12][C:8]2[CH:7]=[C:6]([NH:5][C:3](=[O:4])[C:2]([F:13])([F:14])[F:1])[CH:11]=[CH:10][CH:9]=2)=[C:17]([N+:23]([O-:25])=[O:24])[CH:18]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 677684-Fluoro-3-nitroanilineHCID 23505419Acetamide, 2,2,2-trifluoro-N-(3-hydroxyphenyl)-

Product 1

HCID 86644699N-[3-(4-amino-2-nitrophenoxy)phenyl]-2,2,2-trifluoroacetamideYield 36.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2,2,2-trifluoro-N-(3-hydroxyphenyl)acetamide (5.0 g, 24.4 mmol) and 4-fluoro-3-nitroaniline (3.8 g, 24.4 mmol) in N,N-dimethylformamide (100 mL) was added cesium carbonate (8.0 g, 24.5 mmol), and the mixture was stirred at 120° C. for 16 hr. The reaction mixture was cooled to room temperature, insoluble material was filtered off, and the filtrate was diluted with ethyl acetate (250 mL), washed successively with water (250 mL) and saturated brine (250 mL×2), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=30/70→70/30), and the obtained solution was concentrated under reduced pressure to give the title compound (3.03 g, 36%) as a yellow powder.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationinsoluble material was filtered off
  3. additionthe filtrate was diluted with ethyl acetate (250 mL)
  4. washwashed successively with water (250 mL) and saturated brine (250 mL×2)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationInsoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=30/70→70/30)
  9. concentrationthe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-eecd11b1919c4509bca87daed6d968fe
Source dataset
uspto-grants-2013_07
Patent number
US08497274B2

Reaction notes

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