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

HRID 2058158Notes

Reaction equation

HRID 2058158 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-amineYield 94.2%

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

Sources & evidence

ORD record
ord-2f58a61e7b3c4f33bec6f68a9c7b18c0
Source dataset
uspto-grants-1980_07
Patent number
US04215121

Reaction notes

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