2-(Methylamino)ethanol → 2-(3,4-Dichlorophenyl)-2-[N-(2-hydroxyethyl)-N-methylamino]acetonitrile

HRID 1838

反応式

HRID 1838 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH:5]=O.[C:11]([Si](C)(C)C)#[N:12].[CH3:17][NH:18][CH2:19][CH2:20][OH:21]>CO.[I-].[Zn+2].[I-]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]([N:18]([CH2:19][CH2:20][OH:21])[CH3:17])[C:11]#[N:12])[CH:7]=[CH:8][C:9]=1[Cl:10]

参加物

6

反応物 3

HCID 80162-(Methylamino)ethanolHCID 227103,4-DichlorobenzaldehydeHCID 82115Trimethylsilyl cyanide

生成物 1

HCID 196924572-(3,4-Dichlorophenyl)-2-[N-(2-hydroxyethyl)-N-methylamino]acetonitrile

試薬・触媒・溶媒 2

HCID 9883512zinc(II)iodide触媒HCID 887Methanol溶媒

実験手順

A mixture of 10 g of 3,4-dichlorobenzaldehyde and 9.5 ml of cyanotrimethylsilane is cooled in an ice bath, 0.01 g of zinc iodide is added and the mixture is stirred for 15 minutes at RT. A solution of 4.5 g of 2-(methylamino)ethanol in 50 ml of MeOH is then added and the reaction mixture is heated at 60° C. for 2 hours. After one night at RT, it is concentrated under vacuum, the residue is extracted with ether and the organic phase is washed with water, dried over MgSO4 and filtered. The filtrate is acidified to pH 1 by the addition of a saturated solution of hydrochloric acid in ether, acetone is added and the mixture is stirred until crystallization occurs. This gives 15 g of the expected product after wringing of the crystals formed. M.p.=130° C.

後処理

  1. temperatureis cooled in an ice bath
  2. temperaturethe reaction mixture is heated at 60° C. for 2 hours
  3. waitAfter one night at RT
  4. concentrationit is concentrated under vacuum
  5. extractionthe residue is extracted with ether
  6. washthe organic phase is washed with water
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. additionThe filtrate is acidified to pH 1 by the addition of a saturated solution of hydrochloric acid in ether, acetone
  10. additionis added
  11. stirringthe mixture is stirred until crystallization

出典と根拠

ORDレコード
ord-f2cd038ec84e4a03a81609c6e7029c63
出典データセット
uspto-grants-1998_03
特許番号
US05726313

関連ノート

読み込み中…