2-Chloro-N-(4-methylpyridin-2-yl)acetamide → HCID 54446266, compound

HRID 1973228Notes

Reaction equation

HRID 1973228 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:12])[CH2:10]Cl)[CH:3]=1.[CH3:13][P:14](=[O:25])([O-:24])[O:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1.[K+]>CC(C)=O>[CH3:13][P:14](=[O:24])([O:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)[O:25][CH2:10][C:9]([NH:8][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=1)=[O:12]

Participants

4

Reactant 2

HCID 27767972-Chloro-N-(4-methylpyridin-2-yl)acetamideHCID 86734242HCID 86734242, compound

Product 1

HCID 54446266HCID 54446266, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-(4-Methyl-2-pyridyl)-α-chloroacetamide (18.5 grams), potassium O-(3,4-dichlorophenyl) methylphosphonate (29.5 grams) and acetone (150 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is stirred and heated at reflux for a period of about 18 hours. After this time the reaction mixture is cooled, filtered and stripped of acetone on a steam bath to yield a residue. The residue is extracted with chloroform and the chloroform solution is washed with water. The washed solution is dried over magnesium sulfate, is filtered and evaporated to yield the desired product O-[2-(4-methyl-2-pyridylamino)-2-ketoethyl] O-(3,4-dichlorophenyl) methylphosphonate as the residue.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureheated
  4. temperatureat reflux for a period of about 18 hours
  5. temperatureAfter this time the reaction mixture is cooled
  6. filtrationfiltered
  7. customstripped of acetone on a steam bath
  8. customto yield a residue
  9. extractionThe residue is extracted with chloroform
  10. washthe chloroform solution is washed with water
  11. dry with materialThe washed solution is dried over magnesium sulfate
  12. filtrationis filtered
  13. customevaporated

Sources & evidence

ORD record
ord-a39537213a8f4a1e88e125530bfd38c1
Source dataset
uspto-grants-1976_12
Patent number
US03996352

Reaction notes

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