Triethylamine → HCID 17821889、化合物

HRID 50051ノート

反応式

HRID 50051 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 17821889HCID 17821889、化合物収率 54.2%

試薬・触媒・溶媒 2

HCID 7108Phenothiazine触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-28fc72b09bfd40d38c95cdc20e1e7b8f
出典データセット
uspto-grants-2004_03
特許番号
US06710149B2

反応ノート

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