N,N'-Dimethylethylenediamine → HCID 19418786, compound

HRID 864400Notes

Reaction equation

HRID 864400 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][NH:5][CH3:6].C(=O)([O-])[O-].[K+].[K+].Cl[C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[CH:16][N:15]=1>C(#N)C>[CH3:1][N:2]([C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[CH:16][N:15]=1)[CH2:3][CH2:4][NH:5][CH3:6]

Participants

5

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 19418786HCID 19418786, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of N,N'-dimethylethylenediamine (3.2 ml) and potassium carbonate (830 mg) in acetonitrile (15 ml) stirred at 20°-25° under a nitrogen atmosphere is added a solution of 2-chloro-3-nitropyridine (500 mg) in acetonitrile (10 ml) over one hour. The mixture is concentrated under reduced pressure and partitioned between methylene chloride (75 ml) and water (25 ml). The phases are separated and the aqueous phase is extracted with methylene chloride (25 ml) and the total organics are dried with saline and sodium sulfate. Concentration under reduced pressure gives the title compound, NMR (CDCl3) 8.29, 8.10, 6.69, 3.85, 2.90, 2.88 and 2.46δ.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. custompartitioned between methylene chloride (75 ml) and water (25 ml)
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with methylene chloride (25 ml)
  5. dry with materialthe total organics are dried with saline and sodium sulfate
  6. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-3eeb4df48f174a17b06fe6c5334491a2
Source dataset
uspto-grants-1996_10
Patent number
US05563142

Reaction notes

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