Dimethylformamide → 5-cyano-N-(4-chlorophenyl)-2-methoxybenzamide

HRID 646277Notes

Reaction equation

HRID 646277 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:18][CH3:19])=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)=[O:8].[CH3:20][N:21](C)C=O>[C-]#N.[Zn+2].[C-]#N>[C:20]([C:2]1[CH:3]=[CH:4][C:5]([O:18][CH3:19])=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)=[O:8])#[N:21]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 53460135-bromo-N-(4-chlorophenyl)-2-methoxybenzamide

Product 1

HCID 231414775-cyano-N-(4-chlorophenyl)-2-methoxybenzamideYield 64%

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Procedure

5-Bromo-N-(4-chlorophenyl)-2-methoxybenzamide (9.0 g) obtained in step C, and 7.8 g of zinc cyanide were dissolved in 100 mL of N,N-dimethylformamide. The N,N-dimethylformamide was degassed under reduced pressure, and then the interior of the reactor was purged with nitrogen. After 2.3 g of tetrakistriphenylphosphine palladium was added, the N,N-dimethylformamide was degassed again under reduced pressure, and then the interior of the reactor was purged with argon. This solution was stirred for 2 hours and a half at 100° C., whereafter the solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate. The insolubles were removed by filtration, and washed with ethyl acetate. The filtrate and the washings were combined, 100 mL of water was added, and then the organic layer was separated. The aqueous layer was extracted twice with ethyl acetate. After the respective organic layers were combined, the combined organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was separated by filtration, and then washed with ethyl acetate. The filtrate and the washings were combined, and ethyl acetate was distilled off under reduced pressure. The resulting residue was washed with methanol. The resulting solid was dried under reduced pressure to obtain 4.9 g (64%) of 5-cyano-N-(4-chlorophenyl)-2-methoxybenzamide.

Workup

  1. customThe N,N-dimethylformamide was degassed under reduced pressure
  2. customthe interior of the reactor was purged with nitrogen
  3. additionAfter 2.3 g of tetrakistriphenylphosphine palladium was added
  4. customthe N,N-dimethylformamide was degassed again under reduced pressure
  5. customthe interior of the reactor was purged with argon
  6. distillationa half at 100° C., whereafter the solvent was distilled off under reduced pressure
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. customThe insolubles were removed by filtration
  9. washwashed with ethyl acetate
  10. addition100 mL of water was added
  11. customthe organic layer was separated
  12. extractionThe aqueous layer was extracted twice with ethyl acetate
  13. washthe combined organic layer was washed with a saturated aqueous solution of sodium chloride
  14. dry with materialdried over anhydrous sodium sulfate
  15. customThe anhydrous sodium sulfate was separated by filtration
  16. washwashed with ethyl acetate
  17. distillationethyl acetate was distilled off under reduced pressure
  18. washThe resulting residue was washed with methanol
  19. customThe resulting solid was dried under reduced pressure

Sources & evidence

ORD record
ord-84e0ddffce3e42348675b6ba0127c6a1
Source dataset
uspto-grants-2010_04
Patent number
US07705053B2

Reaction notes

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