Sodium Hydroxide → 2-(2-Dimethylaminoethylamino)-5,6-dimethyl pyrazine

HRID 614310Notes

Reaction equation

HRID 614310 reaction equation
Cl[C:2]1[CH:7]=[N:6][C:5]([CH3:8])=[C:4]([CH3:9])[N:3]=1.[CH3:10][N:11]([CH2:13][CH2:14][NH2:15])[CH3:12].[OH-].[Na+]>O>[CH3:10][N:11]([CH3:12])[CH2:13][CH2:14][NH:15][C:2]1[CH:7]=[N:6][C:5]([CH3:8])=[C:4]([CH3:9])[N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 66053N,N-DimethylethylenediamineHCID 126003905-Chloro-2,3-dimethylpyrazine

Product 1

HCID 233499152-(2-Dimethylaminoethylamino)-5,6-dimethyl pyrazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-chloro-5,6-dimethylpyrazine (12.8 g., 0.09 mole) is added to unsym-dimethylethylenediamine (26 g., 0.295 mole) containing cuprous chloride (0.25 g.) and the mixture is heated for 48 hours in an oil bath maintained at 135°-140° C. On cooling, 50 ml of water and a single molar excess of 10N sodium hydroxide are added. The mixture is extracted with methylene chloride. The organic extracts are backwashed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated under vacuum. The residual oil is dissolved in hexane, filtered and reconcentrated to obtain the product oil (15.8 g., 0.081 mole).

Workup

  1. temperaturethe mixture is heated for 48 hours in an oil bath
  2. temperaturemaintained at 135°-140° C
  3. temperatureOn cooling
  4. extractionThe mixture is extracted with methylene chloride
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. dissolutionThe residual oil is dissolved in hexane
  9. filtrationfiltered
  10. customto obtain the product oil (15.8 g., 0.081 mole)

Sources & evidence

ORD record
ord-717317f935e04e23a2f7aa78fd13bba6
Source dataset
uspto-grants-1979_03
Patent number
US04144338

Reaction notes

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