Potassium Carbonate → HCID 66810431, compound

HRID 1097498Notes

Reaction equation

HRID 1097498 reaction equation
F[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[OH:12][C:13]1[CH:14]=[C:15]([CH:29]=[CH:30][CH:31]=1)[C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1)=[O:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:6][C:5]1[CH:7]=[CH:8][C:2]([O:12][C:13]2[CH:14]=[C:15]([CH:29]=[CH:30][CH:31]=2)[C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=2)=[O:17])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 677684-Fluoro-3-nitroanilineHCID 28391877HCID 28391877, compound

Product 1

HCID 66810431HCID 66810431, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-fluoro-3-nitroaniline (1.0 g, 6.40 mmol) and 3-hydroxy-N-[3-(trifluoromethyl)phenyl]benzamide (1.80 g, 6.40 mmol) in N,N-dimethylformamide (15 mL) was added potassium carbonate (1.32 g, 9.60 mmol), and the mixture was stirred at 100° C. for 14 hr. The reaction mixture was cooled to room temperature, insoluble material was filtered off and washed with ethyl acetate (150 mL). The filtrate and washings were combined and the mixture was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (100 mL), washed successively with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL), 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 basic silica gel column chromatography (ethyl acetate/n-hexane=30/70→100/0), and the obtained solution was concentrated under reduced pressure. The residue was crystallized from ethyl acetate/n-hexane to give the title compound (1.70 g, 64%) as a red-orange powder.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationinsoluble material was filtered off
  3. washwashed with ethyl acetate (150 mL)
  4. concentrationthe mixture was concentrated under reduced pressure
  5. additionThe obtained residue was diluted with ethyl acetate (100 mL)
  6. washwashed successively with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationInsoluble material was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=30/70→100/0)
  11. concentrationthe obtained solution was concentrated under reduced pressure
  12. customThe residue was crystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-c066aa998b364f1980347a2ea229d1d7
Source dataset
uspto-grants-2012_03
Patent number
US08143258B2

Reaction notes

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