Hydrochloric Acid → HCID 20339528, compound

HRID 1395533Notes

Reaction equation

HRID 1395533 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[CH:3]=1.[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19][Cl:20].Cl>CN(C)C=O>[Cl:20][CH2:19][CH2:18][CH2:17][CH2:16][N:9]([C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[N:5]=1)[C:10](=[O:12])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutaneHCID 223262N-(4,6-Dimethylpyridin-2-yl)ethanimidic acid

Product 1

HCID 20339528HCID 20339528, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To N-(4,6-dimethyl-2-pyridyl)acetamide (49.2 g, 0.3 mole) dissolved in dimethylformamide (550 ml) is added sodium hydride in mineral oil (50%) (13.45 g., 0.32 mole) in portions at room temperature. When reaction is complete, the mixture is warmed with stirring to 45° and 1-bromo-4-chlorobutane (52.5 g., 0.306 mole) is added in one portion and stirred one hour on the steam bath. The reaction mixture is then cooled, acidified with hydrochloric acid and concentrated under vacuum. The residue is dissolved in water and extracted with diethyl ether. The aqueous layer is made basic with sodium hydroxide and extracted with ether. The combined etheral extracts are washed with brine, treated with charcoal, dried (sodium sulfate) and concentrated to obtain the product oil, weight 56.6 g.

Workup

  1. customWhen reaction
  2. temperaturethe mixture is warmed
  3. stirringstirred one hour on the steam bath
  4. temperatureThe reaction mixture is then cooled
  5. concentrationconcentrated under vacuum
  6. dissolutionThe residue is dissolved in water
  7. extractionextracted with diethyl ether
  8. extractionextracted with ether
  9. washThe combined etheral extracts are washed with brine
  10. additiontreated with charcoal
  11. dry with materialdried (sodium sulfate)
  12. concentrationconcentrated
  13. customto obtain the product oil, weight 56.6 g

Sources & evidence

ORD record
ord-99968c3d8aee4fd28f24280df718ca60
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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