Potassium Carbonate → HCID 86740646, compound

HRID 1589129Notes

Reaction equation

HRID 1589129 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](=[S:21])(Cl)([O:18][CH3:19])[O:16][CH3:17]>C(#N)C>[CH3:17][O:16][P:15]([O:18][CH3:19])([N:4]=[C:3]([S:5][CH2:6][CH3:7])[N:2]([CH3:8])[CH3:1])=[S:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 17304Dimethyl phosphorochloridothionateHCID 13565740HCID 13565740, compound

Product 1

HCID 86740646HCID 86740646, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 13.2 g of N,N-dimethylcarbamimidothioic acid, ethyl ester, 27.6 g of finely powdered potassium carbonate and 250 ml of acetonitrile, 16.1 g of phosphorochloridothioic acid, O,O-dimethyl ester was added. The mixture was stirred and heated to 40° C. for 4 hours. The salts were removed by filtration and the filtration concentrated in a rotary evaporator. The residue was taken up in methylene chloride, the methylene chloride solution washed thrice with 50 ml portions of water and dried over anhydrous magnesium sulfate. The solvent was removed in a rotary evaporator, leaving 20.0 g of crude product. To remove some lower boiling impurity the sample was placed in a Kugelrohr (bath temperature 95° C., pressure 0.2 mm) for 2 hours. The residue was exhaustively extracted with hexane and the hexane solution concentrated under vacuum, leaving N'-(dimethoxyphosphinothioyl)-N,N-dimethylcarbamimidothioic acid, ethyl ester as a nearly colorless oil. The product has a refractive index of nd25 =1.5610. The IR and NMR spectra were in agreement with the structural assignment.

Workup

  1. additionwas added
  2. customThe salts were removed by filtration
  3. filtrationthe filtration
  4. concentrationconcentrated in a rotary evaporator
  5. washthe methylene chloride solution washed thrice with 50 ml portions of water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed in a rotary evaporator
  8. customleaving 20.0 g of crude product
  9. customTo remove some lower boiling impurity the sample
  10. extractionThe residue was exhaustively extracted with hexane
  11. concentrationthe hexane solution concentrated under vacuum

Sources & evidence

ORD record
ord-a890cf6254d74526965d1b65b3a0c2e5
Source dataset
uspto-grants-1986_02
Patent number
US04568670

Reaction notes

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