Potassium Iodide → O-[1-(4-chlorophenyl)-2-(N,N-diethylcarbamoyloxy)-2-methoxyiminoethyl] O,O-diethyl phosphate

HRID 1578606Notes

Reaction equation

HRID 1578606 reaction equation
Cl[CH:2]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[C:3]([O:7][C:8](=[O:14])[N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[N:4][O:5][CH3:6].[P:22]([O-:30])([O:27][CH2:28][CH3:29])([O:24][CH2:25][CH3:26])=[O:23].[K+].[I-].[K+]>C(C(C)=O)C>[P:22]([O:27][CH2:28][CH3:29])([O:24][CH2:25][CH3:26])([O:30][CH:2]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[C:3]([O:7][C:8](=[O:14])[N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[N:4][O:5][CH3:6])=[O:23]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 23663701Potassium diethyl phosphateHCID 539660661-chloro-1-(4-chlorophenyl)-2-(N,N-diethylcarbamoyloxy)-2-methoxyiminoethane

Product 1

HCID 54133950O-[1-(4-chlorophenyl)-2-(N,N-diethylcarbamoyloxy)-2-methoxyiminoethyl] O,O-diethyl phosphate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

1-Chloro-1-(4-chlorophenyl)-2-(N,N-diethylcarbamoyloxy)-2-methoxyiminoethane (16.6 grams; 0.05 mole), methyl ethyl ketone (100 ml), potassium O,O-diethyl phosphate (9.6 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 12 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 solvents 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-[1-(4-chlorophenyl)-2-(N,N-diethylcarbamoyloxy)-2-methoxyiminoethyl] O,O-diethyl phosphate.

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 12 hours
  5. filtrationis filtered
  6. customto remove inorganic salts
  7. washThe salts are washed with acetone
  8. customThe resulting solution is stripped of solvents 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-e9b43fa232f047fe81cb38d8999d13fb
Source dataset
uspto-grants-1976_02
Patent number
US03937824

Reaction notes

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