Methyl iodide → HCID 86740645, compound

HRID 1589127Notes

Reaction equation

HRID 1589127 reaction equation
[CH3:1][O:2][P:3]([O:13]C)([N:5]=[C:6]([S:10][CH2:11][CH3:12])[N:7]([CH3:9])[CH3:8])=[S:4].[CH3:15]I>CO>[CH3:1][O:2][P:3]([S:13][CH3:15])([N:5]=[C:6]([S:10][CH2:11][CH3:12])[N:7]([CH3:9])[CH3:8])=[O:4]

Participants

4

Reactant 2

HCID 6328Methyl iodide2×HCID 86740646HCID 86740646, compound

Product 1

HCID 86740645HCID 86740645, compoundYield 263.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 36.8 g of N'-(dimethoxyphosphinothioyl)-N,N-dimethylcarbamimidothioic acid, ethyl ester, 120 ml of methanol and 5.0 g of methyl iodide was heated under reflux for 18 hours, then another 5.0 g of methyl iodide was added and heating under reflux was continued for 6 hours. The mixture was concentrated under vacuum, the residue dissolved in methylene chloride, the methylene chloride solution washed once with water and dried over anhydrous magnesium sulfate. The solvent was removed in a rotary evaporator and the residual oil distilled in a Kugelrohr (bath temperature 140° C., pressure 0.3 mm) yielding 23.8 g (65% of theoretical) of N'-(methoxy(methylthio)phosphinyl)-N,N-dimethylcarbamimidothioic acid, ethyl ester. The IR and NMR spectra are in agreement with the assigned structure and identical to those obtained from the compound prepared by the method A.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. temperatureheating
  4. temperatureunder reflux
  5. concentrationThe mixture was concentrated under vacuum
  6. dissolutionthe residue dissolved in methylene chloride
  7. washthe methylene chloride solution washed once with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed in a rotary evaporator
  10. distillationthe residual oil distilled in a Kugelrohr (bath temperature 140° C., pressure 0.3 mm)

Sources & evidence

ORD record
ord-ee856a8fb97241d1ac4c91261582a935
Source dataset
uspto-grants-1986_02
Patent number
US04568670

Reaction notes

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