Water → 5-Cyano-2-ethoxy-N,4-dimethylbenzamide

HRID 1295923Notes

Reaction equation

HRID 1295923 reaction equation
[CH3:1][NH:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8](Br)[C:7]([CH3:11])=[CH:6][C:5]=1[O:12][CH2:13][CH3:14].[C-:16]#[N:17].[Na+].C(OCC)(=O)C.O>C(#N)CC.[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][NH:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([C:16]#[N:17])[C:7]([CH3:11])=[CH:6][C:5]=1[O:12][CH2:13][CH3:14]

Participants

8

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 229298455-Bromo-2-ethoxy-N,4-dimethylbenzamide

Product 1

HCID 229298705-Cyano-2-ethoxy-N,4-dimethylbenzamideYield 58%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 7854PropionitrileSolvent

Procedure

After dissolving N1,4-dimethyl-5-bromo-2-ethoxybenzamide (200 g) in propionitrile (1.51), sodium cyanide (72 g), copper iodide (14 g) and tetrakis(triphenylphosphine)palladium (42 g) were added under a nitrogen atmosphere and the mixture was heated to reflux for 5 hours. Ethyl acetate and water were added and the reaction mixture was filtered through celite. The precipitated crystals in the filtrate were filtered off (15.4 g). This filtrate was then separated and washed with brine. The organic layer was dried over anhydrous magnesium sulfate and was concentrated after filtering off the insoluble portion. The obtained crystals were filtered off and washed with ethyl acetate (77.64 g). The crystals were combined to yield the title compound (93.04 g) as a white solid.

Workup

  1. additionwere added under a nitrogen atmosphere
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 5 hours
  4. filtrationthe reaction mixture was filtered through celite
  5. filtrationThe precipitated crystals in the filtrate were filtered off (15.4 g)
  6. customThis filtrate was then separated
  7. washwashed with brine
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. concentrationwas concentrated
  10. filtrationafter filtering off the insoluble portion
  11. filtrationThe obtained crystals were filtered off
  12. washwashed with ethyl acetate (77.64 g)

Sources & evidence

ORD record
ord-98ee0fdc771c4be2b269a65bdde330ed
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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