N,N'-Dimethylethylenediamine → 2,5-Dimethylbenzonitrile

HRID 2253501

Reaction equation

HRID 2253501 reaction equation
[C-]#N.[Na+].Br[C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[CH3:12].[CH3:13][NH:14]CCNC.[OH-].[NH4+]>[Cu]I.O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:12][C:6]1[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:5]=1[C:13]#[N:14]

Participants

9

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 8929Sodium CyanideHCID 11121Benzene, 2-bromo-1,4-dimethyl-HCID 14923Ammonium Hydroxide

Product 1

HCID 836882,5-Dimethylbenzonitrile

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 (93 mg, 1.898 mmol), dried KI (52 mg, 0.313 mmol, 20 mol %) and CuI (30 mg, 0.158 mmol, 10 mol %), evacuated and backfilled with argon three times. 2-Bromo-1,4-dimethylbenzene (215 μL, 1.557 mmol), N,N′-dimethylethylenediamine (165 μL, 1.549 mmol) and anhydrous toluene (1 mL) were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 24 h. The resulting yellow 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 washed with 1 mL of water and dried over MgSO4. The GC analysis showed consumption of the majority of the starting material, and formation of the title compound (as confirmed by GC-MS).

Workup

  1. customAn oven dried screw
  2. customcap test tube
  3. customevacuated
  4. customThe tube was sealed
  5. temperatureThe resulting yellow suspension was cooled to room temperature
  6. stirringThe mixture was stirred at 25° C. for 10 min
  7. washthe organic layer was washed with 1 mL of water
  8. dry with materialdried over MgSO4
  9. customconsumption of the majority of the starting material, and formation of the title compound (as confirmed by GC-MS)

Sources & evidence

ORD record
ord-1478059c26de4e64809e19a5eef8769c
Source dataset
uspto-grants-2008_01
Patent number
US07323608B2

Linked notes

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