Potassium Carbonate → 3-(1-cyano-1-methylethyl)-N-[3-(2-cyano-4-nitrophenoxy)phenyl]benzamide

HRID 455160Notes

Reaction equation

HRID 455160 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:7][C:8]=1F)#[N:2].[C:13]([C:15]([C:18]1[CH:19]=[C:20]([CH:31]=[CH:32][CH:33]=1)[C:21]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=1)=[O:22])([CH3:17])[CH3:16])#[N:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:13]([C:15]([C:18]1[CH:19]=[C:20]([CH:31]=[CH:32][CH:33]=1)[C:21]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:8]2[CH:7]=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=2[C:1]#[N:2])[CH:25]=1)=[O:22])([CH3:17])[CH3:16])#[N:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5194172-Fluoro-5-nitrobenzonitrileHCID 573868253-(1-cyano-1-methylethyl)-N-(3-hydroxyphenyl)benzamide

Product 1

HCID 668105993-(1-cyano-1-methylethyl)-N-[3-(2-cyano-4-nitrophenoxy)phenyl]benzamideYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-cyano-4-fluoronitrobenzene (1.76 g, 10.5 mmol) and 3-(1-cyano-1-methylethyl)-N-(3-hydroxyphenyl)benzamide (2.97 g, 10.5 mmol) in N,N-dimethylformamide (20 mL) was added potassium carbonate (2.17 g, 15.7 mmol), and the mixture was stirred at 70° C. for 12 hr. The reaction mixture was cooled to room temperature, insoluble material was filtered off, water (100 ml) was added to the filtrate, and the mixture was extracted with ethyl acetate (200 mL). The organic layer was washed with saturated brine (100 mL×2), dried over anhydrous sodium sulfate, and insoluble material was filtered off. The obtained organic layer was purified by basic silica gel column chromatography (eluate: ethyl acetate), and the obtained solution was concentrated under reduced pressure to give the title compound (4.21 g, 94%) as a yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationinsoluble material was filtered off
  3. additionwater (100 ml) was added to the filtrate
  4. extractionthe mixture was extracted with ethyl acetate (200 mL)
  5. washThe organic layer was washed with saturated brine (100 mL×2)
  6. dry with materialdried over anhydrous sodium sulfate, and insoluble material
  7. filtrationwas filtered off
  8. customThe obtained organic layer was purified by basic silica gel column chromatography (eluate: ethyl acetate)
  9. concentrationthe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0500a04f6eb34a03ae243c3c67125a96
Source dataset
uspto-grants-2013_07
Patent number
US08497274B2

Reaction notes

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