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Potassium Iodide → O-[2-(N-cyclopropylcarbamoyloxy)-2-ethoxyiminoethyl] 2-methylphenyl(4-bromophenyl)thionophosphinate

HRID 1578595
Notes
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Reaction equation

HRID 1578595 reaction equation
Cl[CH2:2][C:3]([O:8][C:9](=[O:14])[NH:10][CH:11]1[CH2:13][CH2:12]1)=[N:4][O:5][CH2:6][CH3:7].[CH3:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([C:26]1[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][CH:27]=1)=[P:23](=[O:25])[O-:24].[K+].[I-].[K+]>C(C(C)=O)C>[CH3:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([C:26]1[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][CH:27]=1)=[P:23](=[O:24])[O:25][CH2:2][C:3]([O:8][C:9](=[O:14])[NH:10][CH:11]1[CH2:13][CH2:12]1)=[N:4][O:5][CH2:6][CH3:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 543801311-chloro-2-(N-cyclopropylcarbamoyloxy)-2-ethoxyiminoethaneHCID 131710027Potassium 2-methylphenyl(4-bromophenyl)thionophosphinate

Product 1

HCID 131710026O-[2-(N-cyclopropylcarbamoyloxy)-2-ethoxyiminoethyl] 2-methylphenyl(4-bromophenyl)thionophosphinate

Reagents, catalysts & solvents 1

HCID 6569
Methyl Ethyl Ketone
Solvent

Procedure

1-Chloro-2-(N-cyclopropylcarbamoyloxy)-2-ethoxyiminoethane (11 grams; 0.05 mole), methyl ethyl ketone (80 ml), potassium 2-methylphenyl(4-bromophenyl)thionophosphinate (17 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 8 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-[2-(N-cyclopropylcarbamoyloxy)-2-ethoxyiminoethyl] 2-methylphenyl(4-bromophenyl)thionophosphinate.

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 8 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-830f603568f34fc589cc0d95b0dd9c6f
Source dataset
uspto-grants-1976_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03937824

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes