Dimethylamine → 6-Chloro-N,N-dimethylpyrazin-2-amine

HRID 614311Notes

Reaction equation

HRID 614311 reaction equation
[CH3:1][NH:2][CH3:3].Cl[C:5]1[CH:10]=[N:9][CH:8]=[C:7]([Cl:11])[N:6]=1>C(O)(C)C>[Cl:11][C:7]1[CH:8]=[N:9][CH:10]=[C:5]([N:2]([CH3:3])[CH3:1])[N:6]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 785042,6-Dichloropyrazine

Product 1

HCID 232734436-Chloro-N,N-dimethylpyrazin-2-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Cuprous chloride (50 mg) is added to a solution of dimethylamine (36 g., 0.8 mole) in 260 ml of isopropanol. 2,6-Dichloropyrazine (49.9 g., 0.33 mole) is added to the mixture with stirring and cooling to maintain the temperature at 35°-40° C. After 3/4 hr. the cooling bath is removed and the reaction mixture is stored at ambient temperature for 16 hours and finally at 42°-48° C. for 3 hours. The solvent is removed under vacuum and the residue is dissolved in dilute hydrochloric acid. The aqueous solution is extracted with ether and then made basic with solid sodium bicarbonate and extracted with methylene chloride. The organic extracts are washed with brine, dried over sodium sulfate and concentrated under vacuum to obtain 49 g. of product, melting point 46°-8° C.

Workup

  1. temperaturecooling
  2. temperatureto maintain the temperature at 35°-40° C
  3. waitAfter 3/4 hr
  4. customthe cooling bath is removed
  5. customThe solvent is removed under vacuum
  6. dissolutionthe residue is dissolved in dilute hydrochloric acid
  7. extractionThe aqueous solution is extracted with ether
  8. extractionextracted with methylene chloride
  9. washThe organic extracts are washed with brine
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated under vacuum
  12. customto obtain 49 g

Sources & evidence

ORD record
ord-b6ee49adc6c44d49a5c6d75734795ead
Source dataset
uspto-grants-1979_03
Patent number
US04144338

Reaction notes

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