Dimethylformamide → HCID 68814479, compound

HRID 732472Notes

Reaction equation

HRID 732472 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[F:17])[C:5]([N:7]([CH2:11][CH2:12][CH3:13])[CH2:8][CH2:9][CH3:10])=[O:6].[CH3:18][N:19](C=O)C>[Cu]>[C:18]([C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[F:17])[C:5]([N:7]([CH2:11][CH2:12][CH3:13])[CH2:8][CH2:9][CH3:10])=[O:6])#[N:19]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 68815861HCID 68815861, compound

Product 1

HCID 68814479HCID 68814479, compound

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

Combine 3-bromo-4-fluoro-N,N-dipropylbenzamide (1.0 g, 3.3 mmol) with copper cyamide (0.45 g, 5.0 mmol) in DMF (5 mL) and heat at reflux until all starting material is consumed. Cool to room temperature and partition between ethyl acetate and saturated aqueous sodium bicarbonate. Separate the organic layer and wash with saturated aqueous sodium bicarbonate, saturated sodium chloride solution, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 20:80 ethyl acetate:hexanes) to give the title compound.

Workup

  1. temperatureat reflux until all starting material
  2. customis consumed
  3. custompartition between ethyl acetate and saturated aqueous sodium bicarbonate
  4. customSeparate the organic layer
  5. washwash with saturated aqueous sodium bicarbonate, saturated sodium chloride solution
  6. dry with materialdry (magnesium sulfate)
  7. concentrationconcentrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 20:80 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-b9a66073728b4ed6add58e89abc263d2
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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