Potassium Carbonate → HCID 86740645, compound

HRID 1589128Notes

Reaction equation

HRID 1589128 reaction equation
[CH3:1][N:2]([CH3:8])[C:3]([S:5][CH2:6][CH3:7])=[NH:4].C(=O)([O-])[O-].[K+].[K+].[P:15](=[O:21])(Cl)([S:18][CH3:19])[O:16][CH3:17]>C(#N)C>[CH3:17][O:16][P:15]([S:18][CH3:19])([N:4]=[C:3]([S:5][CH2:6][CH3:7])[N:2]([CH3:8])[CH3:1])=[O:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13358089O,S-Dimethyl phosphorochloridothioateHCID 13565740HCID 13565740, compound

Product 1

HCID 86740645HCID 86740645, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 6.6 g of N,N-dimethylcarbamimidothioic acid, ethyl ester, 8.0 g of finely powdered potassium carbonate and 50 ml of acetonitrile was added dropwise 8.0 g of phosphorochloridothioic acid, O,S-dimethyl ester. The mixture was stirred until no starting material could be detected by GLC (Gas Liquid Chromatography). The salts were then removed by filtration, the filtrate concentrated under vacuum, the residue taken up in ether, the ether solution washed once with water, once with 5% aqueous sodium hydroxide, once with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under vacuum and the residue distilled in a Kugelrohr (bath temperature 140° C., pressure 0.3 mm) yielding 8.2 g (64% of theoretical) of N'-(methoxy(methylthio)phosphinyl)-N,N-dimethylcarbamimidothioic acid, ethyl ester as a colorless oil. The IR and NMR spectra are identical to those obtained from the compound prepared by method A.

Workup

  1. customThe salts were then removed by filtration
  2. concentrationthe filtrate concentrated under vacuum
  3. washthe ether solution washed once with water, once with 5% aqueous sodium hydroxide, once with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under vacuum
  6. distillationthe residue distilled in a Kugelrohr (bath temperature 140° C., pressure 0.3 mm)

Sources & evidence

ORD record
ord-87b5485df89b47b6a0be85133dcda850
Source dataset
uspto-grants-1986_02
Patent number
US04568670

Reaction notes

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