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

HRID 1838

반응식

HRID 1838 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 9883512zinc(II)iodide촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f2cd038ec84e4a03a81609c6e7029c63
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726313

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