Sodium Methoxide → HCID 20339555, compound

HRID 1395537Notes

Reaction equation

HRID 1395537 reaction equation
[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8](Cl)[N:7]=1.[CH3:14][O-:15].[Na+]>CN(C)C=O>[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:15][CH3:14])[N:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 20339561N~2~-(6-Chloropyridin-2-yl)-N~1~,N~1~-dimethylethane-1,2-diamine

Product 1

HCID 20339555HCID 20339555, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(2-dimethylaminoethylamino)-6-chloropyridine (10.0 g, 0.05 mole) in dimethylformamide (50 ml) containing sodium methoxide (3.5 gm, 0.065 mole) is heated at 110°-120° for two hours. The solution is cooled and the sodium chloride filtered. After removing the solvent in vacuo, the residue is dissolved in dilute hydrochloric acid (10%), washed with methylene chloride, made alkaline with sodium carbonate and the product is extracted into methylene chloride. After drying this solution over anhydrous sodium sulfate and filtering through charcoal, the solvent is removed under vacuum to give the oily product (7.9 g). This is used without further purification in the succeeding step.

Workup

  1. temperatureis heated at 110°-120° for two hours
  2. temperatureThe solution is cooled
  3. filtrationthe sodium chloride filtered
  4. customAfter removing the solvent in vacuo
  5. dissolutionthe residue is dissolved in dilute hydrochloric acid (10%)
  6. washwashed with methylene chloride
  7. extractionthe product is extracted into methylene chloride
  8. dry with materialAfter drying this solution over anhydrous sodium sulfate
  9. filtrationfiltering through charcoal
  10. customthe solvent is removed under vacuum

Sources & evidence

ORD record
ord-21dd9ff70d834e4cb6a093ee6610dbf6
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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