p-Fluoronitrobenzene → 3-(1-cyano-1-methylethyl)-N-[2-methyl-5-(4-nitrophenoxy)phenyl]benzamide

HRID 2190378Notes

Reaction equation

HRID 2190378 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:11]([C:13]([C:16]1[CH:17]=[C:18]([CH:30]=[CH:31][CH:32]=1)[C:19]([NH:21][C:22]1[CH:27]=[C:26]([OH:28])[CH:25]=[CH:24][C:23]=1[CH3:29])=[O:20])([CH3:15])[CH3:14])#[N:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:11]([C:13]([C:16]1[CH:17]=[C:18]([CH:30]=[CH:31][CH:32]=1)[C:19]([NH:21][C:22]1[CH:27]=[C:26]([O:28][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH:25]=[CH:24][C:23]=1[CH3:29])=[O:20])([CH3:15])[CH3:14])#[N:12]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 673120273-(1-cyano-1-methylethyl)-N-(5-hydroxy-2-methylphenyl)benzamide

Product 1

HCID 673136803-(1-cyano-1-methylethyl)-N-[2-methyl-5-(4-nitrophenoxy)phenyl]benzamideYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-fluoro-4-nitrobenzene (1.26 g, 8.92 mmol) and 3-(1-cyano-1-methylethyl)-N-(5-hydroxy-2-methylphenyl)benzamide (2.50 g, 8.5 mmol) in N,N-dimethylformamide (20 mL) was added potassium carbonate (1.85 g, 13.3 mmol) and the mixture was stirred at 60° C. for 4 hr, and further at 70° C. for 12 hr. The reaction mixture was cooled to room temperature, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (200 ml), washed with 5% aqueous sodium hydrogencarbonate solution (100 mL) and saturated brine (100 mL) successively, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (3.41 g, 97%) as a yellow amorphous substance. The obtained compound was used in the next reaction without a further purification.

Workup

  1. waitfurther at 70° C. for 12 hr
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationthe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionThe obtained residue was diluted with ethyl acetate (200 ml)
  6. washwashed with 5% aqueous sodium hydrogencarbonate solution (100 mL) and saturated brine (100 mL) successively
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe insoluble material was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fdfe283f68514d8eb29557ce7c6bba8f
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

Loading…