Chloroacetonitrile → ethyl (cyanomethyl)methylphosphinate

HRID 1200271Notes

Reaction equation

HRID 1200271 reaction equation
Cl[CH2:2][C:3]#[N:4].[CH3:5][P:6](=O)([O:10]CC)[O:7][CH2:8][CH3:9]>>[C:3]([CH2:2][P:6]([CH3:5])(=[O:10])[O:7][CH2:8][CH3:9])#[N:4]

Participants

3

Reactant 2

HCID 7856Chloroacetonitrile2×HCID 12685Diethyl methylphosphonate

Product 1

HCID 3943037ethyl (cyanomethyl)methylphosphinateYield 95%

Conditions

Temperature
125 °C

Procedure

226.5 g (3 mol) of chloroacetonitrile were heated to 60° C. 470 g (3.53 mol) of diethyl methylphosphonate were added dropwise over a period of 3 hours at 70° to 80° C. During this step heating was not necessary; the reaction was exothermic. Ethyl chloride was collected in a down-stream cold trap. After the dropwise addition was finished, the mixture was slowly heated to 125° C. and kept at this temperature until no more waste gas (ethyl chloride) could be detected. The mixture was subsequently cooled and distilled through a column under an aspirator vacuum to give 418 g of ethyl cyanomethtylmethylphosphinate (b.p. 108°-109° C., 0.0133 kPa). This correspnds to a yield of 95% of theory, based on the amount of chloroacetonitrile used. ##STR4##

Workup

  1. temperatureDuring this step heating
  2. customEthyl chloride was collected in a down-stream cold trap
  3. additionAfter the dropwise addition
  4. temperatureThe mixture was subsequently cooled
  5. distillationdistilled through a column under an aspirator vacuum
  6. customto give 418 g of ethyl cyanomethtylmethylphosphinate (b.p. 108°-109° C., 0.0133 kPa)

Sources & evidence

ORD record
ord-f9571217a2da4537a2e016576f6ceba2
Source dataset
uspto-grants-1990_02
Patent number
US04904813

Reaction notes

Loading…