Pyridine → Di-(2-ethylthioethyl)2-chloroethanephosphonate

HRID 1449302Notes

Reaction equation

HRID 1449302 reaction equation
[Cl:1][CH2:2][CH2:3][P:4](Cl)(Cl)=[O:5].[CH2:8]([S:10][CH2:11][CH2:12][OH:13])[CH3:9].N1[CH:19]=[CH:18]C=CC=1>CCOCC>[CH2:8]([S:10][CH2:11][CH2:12][O:13][P:4]([CH2:3][CH2:2][Cl:1])(=[O:5])[O:13][CH2:12][CH2:11][S:10][CH2:18][CH3:19])[CH3:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 80752-(Ethylthio)ethanolHCID 69645(2-Chloroethyl)phosphonic dichloride

Product 1

HCID 85916432Di-(2-ethylthioethyl)2-chloroethanephosphonate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 18.1 g (0.1 mol) of 2-chloroethane phosphonic acid dichloride in 150 ml of absolute ether is added dropwise with stirring a solution of 21.2 g (0.2 mol) of hydroxyethyl ethyl sulphide and 15.8 g of absolute pyridine in 100 ml of absolute ether at room temperature, during which the temperature increases to 35° and crystallisation occurs. Stirring is continued for a further 14 hours at 25° after which the crystals are removed by filtration and the ethereal filtrate is washed to neutrality with 5% hydrogen carbonate solution and water. It is dried and evaporated and further dried by rotation under high vacuum for 2 hours. A yellow oil is obtained having the following characterisation data:

Workup

  1. temperatureduring which the temperature increases to 35°
  2. customcrystallisation
  3. customafter which the crystals are removed by filtration
  4. washthe ethereal filtrate is washed
  5. customIt is dried
  6. customevaporated
  7. customfurther dried by rotation under high vacuum for 2 hours
  8. customA yellow oil is obtained

Sources & evidence

ORD record
ord-13e9384b72ff4f8c82a8c6f56f8594b2
Source dataset
uspto-grants-1980_02
Patent number
US04190430

Reaction notes

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