Diethyl chlorophosphate → 1-[Ethoxy(isothiocyanato)phosphoryl]oxyethane

HRID 1732863Notes

Reaction equation

HRID 1732863 reaction equation
[S-:1][C:2]#[N:3].[Na+].[P:5](Cl)(=[O:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8]>C1(C)C=CC=CC=1>[CH2:7]([O:6][P:5]([N:3]=[C:2]=[S:1])([O:9][CH2:10][CH3:11])=[O:12])[CH3:8]

Participants

4

Reactant 2

HCID 13139Diethyl chlorophosphateHCID 516871Sodium thiocyanate

Product 1

HCID 5568321-[Ethoxy(isothiocyanato)phosphoryl]oxyethane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 8.02 g of dry sodium thiocyanate in 100 ml of dry toluene at 0° C., under a nitrogen atmosphere is added 13.1 ml (16.6 g) of diethyl phosphorchloridate dropwise with stirring. The mixture is warmed to ambient temperature and stirred 20 hours. The mixture is filtered through a pad of Celite and the pad is washed with two 50 ml portions of toluene. The filtrate is washed with 50 ml of ice cold 10% sodium bicarbonate solution, 50 ml of ice water and dried over anhydrous magnesium sulfate. The mixture is filtered and the filtrate used without further purification is subsequent reaction.

Workup

  1. stirringstirred 20 hours
  2. filtrationThe mixture is filtered through a pad of Celite
  3. washthe pad is washed with two 50 ml portions of toluene
  4. washThe filtrate is washed with 50 ml of ice cold 10% sodium bicarbonate solution, 50 ml of ice water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe mixture is filtered
  7. customthe filtrate used without further purification
  8. customreaction

Sources & evidence

ORD record
ord-018769f105f6407c86ac1455f14fd641
Source dataset
uspto-grants-1980_12
Patent number
US04239708

Reaction notes

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