Ethanol → HCID 20339554, compound

HRID 1395529Notes

Reaction equation

HRID 1395529 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10](=O)[CH3:11])[CH:3]=1.[H-].[Na+].Cl.[CH2:16]([N:18](CCCl)[CH2:19][CH3:20])[CH3:17].C(O)C>CN(C)C=O.C(O)(=O)C>[CH2:16]([N:18]([CH2:19][CH3:20])[CH2:11][CH2:10][NH:9][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[N:5]=1)[CH3:17]

Participants

7

Reactant 4

HCID 702EthanolHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 24758Sodium hydride2×HCID 223262N-(4,6-Dimethylpyridin-2-yl)ethanimidic acid

Product 1

HCID 20339554HCID 20339554, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To 32.8 g (0.2 m) N-(4,6-dimethyl-2-pyridyl)acetamide dissolved in 300 ml dimethylformamide, sodium hydride (50%) (9.67 g 0.21 m) is added at 30°-40° in three portions with stirring. Ten minutes after this addition diethylaminoethylchloride hydrochloride (37.2 g, 0.216 m) is added and the mixture stirred 20 minutes. Sodium hydride (50%) (10.55 g, 0.229 M) is added in three portions at 40°-45°, the mixture stirred at 50°-55° for 1/2 hour and finally at 90° for 21/2 hours. On cooling ethanol, 50 ml. followed by acetic acid, 25 ml, are added. The mixture is concentrated under vacuum, the residue dissolved in dilute hydrochloric acid, and extracted with hexane. The aqueous is made alkaline with sodium hydroxide, 10 N and extracted with methylene chloride. The organic extracts are washed with water, concentrated and the residue distilled. The fraction distilling at 127°-140°/1.3 mm, weight 35.5 g is collected, hydrolyzed by refluxing in sulfuric acid (85 ml), water (80 ml) and acetic acid (170 ml) for 18 hours. The mixture is cooled in an ice bath and sodium hydroxide solution equivalent to the sulfuric acid is added. Ethanol is added and the salts filtered off. The filtrate is concentrated under vacuum and the residue taken up in dilute sodium hydroxide. The mixture is extracted with methylene chloride, the organic extracts washed with brine, dried over sodium sulfate and concentrated to obtain the 2-(2-diethylaminoethylamino)-4,6-dimethylpyridine as an oil, weight 30 g.

Workup

  1. additionis added
  2. stirringthe mixture stirred 20 minutes
  3. stirringthe mixture stirred at 50°-55° for 1/2 hour and finally at 90° for 21/2 hours
  4. additionare added
  5. concentrationThe mixture is concentrated under vacuum
  6. dissolutionthe residue dissolved in dilute hydrochloric acid
  7. extractionextracted with hexane
  8. extractionextracted with methylene chloride
  9. washThe organic extracts are washed with water
  10. concentrationconcentrated
  11. distillationthe residue distilled
  12. distillationThe fraction distilling at 127°-140°/1.3 mm, weight 35.5 g
  13. customis collected
  14. temperatureby refluxing in sulfuric acid (85 ml)
  15. temperatureThe mixture is cooled in an ice bath
  16. additionsodium hydroxide solution equivalent to the sulfuric acid is added
  17. additionEthanol is added
  18. filtrationthe salts filtered off
  19. concentrationThe filtrate is concentrated under vacuum
  20. extractionThe mixture is extracted with methylene chloride
  21. washthe organic extracts washed with brine
  22. dry with materialdried over sodium sulfate
  23. concentrationconcentrated

Sources & evidence

ORD record
ord-1fd37dd14f014a378cc90e71b7b09758
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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