Sodium hydride → HCID 20339625, compound

HRID 1395536Notes

Reaction equation

HRID 1395536 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]([O:23][CH2:24][CH2:25][N:26](C)[CH2:27]CCl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([O:23][CH2:24][CH2:25][N:26]([CH2:11][CH2:10][NH:9][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[N:5]=1)[CH3:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 223262N-(4,6-Dimethylpyridin-2-yl)ethanimidic acidHCID 70589242HCID 70589242, compound

Product 1

HCID 20339625HCID 20339625, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 24.5 g (0.149 mole) of N-(4,6-dimethyl-2-pyridyl)acetamide dissolved in 350 ml of dimethylformamide is added sodium hydride in mineral oil (50%) (7.2 g., 0.15 mole) in two portions with stirring, at room temperature. When reaction ceases, N-(2-benzyloxyethyl)-N-(2-chloroethyl)methylamine hydrochloride (24.5 g., 0.149 mole) is added in 2 portions. After bubbling ceases, the mixture is stirred at 50°-55° for 45 minutes and than heated on a steam bath for two hours. The mixture is cooled and concentrated under vacuum after 25 ml of acetic acid is added. The residue is taken up in dilute hydrochloric acid and extracted with hexane. The aqueous is made alkaline with 10 N sodium hydroxide and extracted with ether, then methylene chloride. The combined organic extracts are backwashed with brine, dried (sodium sulfate) and vacuum concentrated. The residue is distilled, the fraction boiling at 205°-215°/0.5 mm collected and this then refluxed in 5 N sodium hydroxide until hydrolysis is complete. On cooling, the mixture is extracted with toluene and then with methylene chloride. The combined organic extracts are washed with brine, dried and vacuum concentrated to obtain the product as an oil, weight 35 g.

Workup

  1. customWhen reaction
  2. customAfter bubbling ceases
  3. stirringthe mixture is stirred at 50°-55° for 45 minutes
  4. temperaturethan heated on a steam bath for two hours
  5. temperatureThe mixture is cooled
  6. concentrationconcentrated under vacuum after 25 ml of acetic acid
  7. additionis added
  8. extractionextracted with hexane
  9. extractionextracted with ether
  10. dry with materialdried (sodium sulfate) and vacuum
  11. concentrationconcentrated
  12. distillationThe residue is distilled
  13. customthe fraction boiling at 205°-215°/0.5 mm collected
  14. temperaturethis then refluxed in 5 N sodium hydroxide until hydrolysis
  15. temperatureOn cooling
  16. extractionthe mixture is extracted with toluene
  17. washThe combined organic extracts are washed with brine
  18. customdried
  19. concentrationvacuum concentrated

Sources & evidence

ORD record
ord-fd13a70f46204ad0a55ff84739ceb8c8
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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