Potassium Iodide → HCID 54281004, compound

HRID 1578603Notes

Reaction equation

HRID 1578603 reaction equation
Cl[CH2:2][C:3]([O:7][C:8](=[O:12])[N:9]([CH3:11])[CH3:10])=[N:4][O:5][CH3:6].[CH3:13][C:14]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:15]=1[CH2:16][P:17](=[O:22])([O-:21])[O:18][CH2:19][CH3:20].[K+].[I-].[K+]>C(C(C)=O)C>[CH3:13][C:14]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:15]=1[CH2:16][P:17](=[O:21])([O:18][CH2:19][CH3:20])[O:22][CH2:2][C:3]([O:7][C:8](=[O:12])[N:9]([CH3:11])[CH3:10])=[N:4][O:5][CH3:6]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 23720951HCID 23720951, compoundHCID 53919230HCID 53919230, compound

Product 1

HCID 54281004HCID 54281004, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

1-Chloro-2-(N,N-dimethylcarbamoyloxy)-2-methoxyiminoethane (10grams; 0.05 mole), methyl ethyl ketone (60ml), potassium O-ethyl 2-methyl-4-chlorobenzylphosphonate (15.6 grams; 0.05 mole) and a few crystals of potassium iodide are charged into a glass reaction flask equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is then heated at reflux for a period of about 4 hours. After this time the reaction mixture is cooled to room temperature and is filtered to remove inorganic salts. The salts are washed with acetone and the washings combined with the filtrate. The resulting solution is stripped of solvent in a rotary evaporator. The remaining residue is dissolved in ether and the ether solution is washed with water and dried over anhydrous magnesium sulfate. The dried solution is filtered and stripped of ether to yield the desired product O-[2-(N,,N-dimethylcarbamoyloxy)-2-methoxyiminoethyl] O-ethyl 2-methyl-4-chlorobenzylphosphonate.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureThe reaction mixture is then heated
  4. temperatureat reflux for a period of about 4 hours
  5. filtrationis filtered
  6. customto remove inorganic salts
  7. washThe salts are washed with acetone
  8. customThe resulting solution is stripped of solvent in a rotary evaporator
  9. dissolutionThe remaining residue is dissolved in ether
  10. washthe ether solution is washed with water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationThe dried solution is filtered

Sources & evidence

ORD record
ord-d346a2d87bac47149b0ef7c95a3f1bd9
Source dataset
uspto-grants-1976_02
Patent number
US03937824

Reaction notes

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