N,N'-Dimethylethylenediamine → Acetamide, N-(4-cyano-2-fluorophenyl)-

HRID 2180660Notes

Reaction equation

HRID 2180660 reaction equation
[C-]#N.[Na+].Br[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[C:7]([F:15])[CH:6]=1.[CH3:16][NH:17]CCNC.[OH-].[NH4+]>[Cu]I.O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:16]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[C:7]([F:15])[CH:6]=1)#[N:17]

Participants

9

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 8929Sodium CyanideHCID 14923Ammonium HydroxideHCID 67593N-(4-bromo-2-fluorophenyl)acetamide

Product 1

HCID 11344323Acetamide, N-(4-cyano-2-fluorophenyl)-Yield 90%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

An oven dried screw cap test tube was charged with NaCN (137 mg, 2.796 mmol) dried KI (77 mg, 0.464 mmol, 20 mol %) and CuI (44 mg, 0.231 mmol, 10 mol %), N-(4-Bromo-2-fluoro-phenyl)-acetamide (540 mg, 2.330 mmol), evacuated and backfilled with argon three times. Anhydrous toluene (1.550 mL) and N,N′-dimethylethylenediamine (250 μl, 2.348 mmol) were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 24 h. The resulting yellow color suspension was cooled to room temperature, 2 mL of ethyl acetate, 1 mL of ammonium hydroxide 30% and 1 mL of water were added. The mixture was stirred at 25° C. for 10 min then the organic layer was separated and the aqueous layer was extracted three times with ethyl acetate (3×2 mL). The organic layers combined were washed with 5 mL of water and dried over MgSO4. The solvent was removed at reduced pressure. Purification of the residue by flash chromatography on silica gel (2×15 cm; hexane/ethyl acetate 10:1) provided 372 mg (90% yield) of the title compound as a pale yellow solid.

Workup

  1. customAn oven dried screw
  2. customcap test tube
  3. customevacuated
  4. customThe tube was sealed
  5. temperatureThe resulting yellow color suspension was cooled to room temperature
  6. stirringThe mixture was stirred at 25° C. for 10 min
  7. customthe organic layer was separated
  8. extractionthe aqueous layer was extracted three times with ethyl acetate (3×2 mL)
  9. washThe organic layers combined were washed with 5 mL of water
  10. dry with materialdried over MgSO4
  11. customThe solvent was removed at reduced pressure
  12. customPurification of the residue by flash chromatography on silica gel (2×15 cm; hexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-16bb7567d70f4634acaf663fa40318bf
Source dataset
uspto-grants-2005_05
Patent number
US06888032B2

Reaction notes

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