N,N'-Dimethylethylenediamine → HCID 66922323, compound

HRID 2039865Notes

Reaction equation

HRID 2039865 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([O:10][C:11]1[CH:12]=[C:13]2[NH:19][CH:18]=[CH:17][C:14]2=[N:15][CH:16]=1)[CH3:9].[Cl-].[Li+].CNCCNC.C(=O)([O-])[O-].[K+].[K+].[OH-].[NH4+]>CN(C=O)C.[Cu]I.CC(=O)OCC>[CH2:8]([O:10][C:11]1[CH:12]=[C:13]2[N:19]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:18]=[CH:17][C:14]2=[N:15][CH:16]=1)[CH3:9]

Participants

10

Reactant 6

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 14923Ammonium HydroxideHCID 433294Lithium ChlorideHCID 66922424HCID 66922424, compound

Product 1

HCID 66922323HCID 66922323, compoundYield 77.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Iodobenzene (5.85 ml, 28.7 mmol) was added to a mixture of the compound of step 2 (3 g, 18.5 mmol), copper(I) iodide (387.6 mg, 2.04 mmol), lithium chloride (941.1 mg, 22.2 mmol), N,N′-dimethylethylenediamine (505.5 mg, 5.74 mmol) and potassium carbonate (9.10 g, 65.9 mmol) in DMF (50 ml). The reaction mixture was stirred at 120° C. for 6 h. After cooling to room temperature, a solution of ammonium hydroxide (10% in water) and EA were added. The organic layer was separated, washed twice with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (EA/HEP) to give 3.40 g of the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe organic layer was separated
  3. washwashed twice with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (EA/HEP)

Sources & evidence

ORD record
ord-94cf39248cf041aca5a64831b2d26d1f
Source dataset
uspto-grants-2013_11
Patent number
US08580813B2

Reaction notes

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