Triethylamine → HCID 17821889, 화합물

HRID 50051노트

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HRID 50051 반응식
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]

참가 물질

6

반응물 3

HCID 8471Triethylamine2회HCID 243082-(Chloromethyl)-2-propenenitrile2회HCID 2733833Dimethyl (2-hydroxyethyl)phosphonate

생성물 1

HCID 17821889HCID 17821889, 화합물수율 54.2%

시약·촉매·용매 2

HCID 7108Phenothiazine촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
65 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-28fc72b09bfd40d38c95cdc20e1e7b8f
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710149B2

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