Triethylamine → HCID 17821889, compound

HRID 50051Notes

Reaction equation

HRID 50051 reaction equation
Cl[CH2:2][C:3](=[CH2:6])[C:4]#[N:5].[CH3:7][O:8][P:9]([CH2:13][CH2:14][OH:15])(=[O:12])[O:10][CH3:11].C(N(CC)CC)C>C1COCC1.C1C2NC3C(=CC=CC=3)SC=2C=CC=1>[CH3:7][O:8][P:9]([CH2:13][CH2:14][O:15][CH2:2][C:3](=[CH2:6])[C:4]#[N:5])([O:10][CH3:11])=[O:12]

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 243082-(Chloromethyl)-2-propenenitrile2×HCID 2733833Dimethyl (2-hydroxyethyl)phosphonate

Product 1

HCID 17821889HCID 17821889, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 7108PhenothiazineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

86.3 g (850 mmol) 2-(chloromethyl)-acrylonitrile are added dropwise at room temperature to a solution of 130.9 g (850 mmol) 2-hydroxyethylphosphonic acid dimethylester, 85.9 g (850 mmol) triethylamine (TEA) and 40 mg phenothiazine (stabilizer) in 1 l THF. Subsequently, the mixture is heated for 6 hours at 65° C. under reflux. 9.1 g (90 mmol) TEA and 9.1 g (90 mmol) 2-(chloromethyl)-acrylonitrile are once again added one after the other and the mixture is heated for a further 24 hours under reflux. After the reaction mixture has cooled, the formed deposit of TEA hydrochloride is filtered out and is washed twice with 50 ml THF. After the THF phases have been concentrated on the rotary evaporator, the residual raw product is taken up in 650 ml methylene chloride and washed twice with water. After it has been dried over anhydrous sodium sulphate, the mixture is concentrated and the residual liquid undergoes fractional distillation in the fine vacuum. 101.0 g (54% yield) of a colourless liquid results at b.p. 150° C. (0.05 mbar).

Workup

  1. temperatureunder reflux
  2. temperatureis heated for a further 24 hours
  3. temperatureunder reflux
  4. temperatureAfter the reaction mixture has cooled
  5. filtrationthe formed deposit of TEA hydrochloride is filtered out and
  6. washis washed twice with 50 ml THF
  7. concentrationAfter the THF phases have been concentrated on the rotary evaporator
  8. washwashed twice with water
  9. dry with materialAfter it has been dried over anhydrous sodium sulphate
  10. concentrationthe mixture is concentrated
  11. distillationdistillation in the fine vacuum

Sources & evidence

ORD record
ord-28fc72b09bfd40d38c95cdc20e1e7b8f
Source dataset
uspto-grants-2004_03
Patent number
US06710149B2

Reaction notes

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