Ammonia → 2-(2-Diisopropylamino ethyl) 3,3-dimethyl 2-(2-pyridyl) pentane-dinitrile

HRID 2414075

반응식

HRID 2414075 반응식
[NH2-].[Na+].N.[CH:4]([N:7]([CH:19]([CH3:21])[CH3:20])[CH2:8][CH2:9][CH:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:11]#[N:12])([CH3:6])[CH3:5].[CH3:22][C:23]([CH3:27])=[CH:24][C:25]#[N:26]>CCOCC.O>[CH:19]([N:7]([CH:4]([CH3:6])[CH3:5])[CH2:8][CH2:9][C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)([C:23]([CH3:27])([CH3:22])[CH2:24][C:25]#[N:26])[C:11]#[N:12])([CH3:21])[CH3:20]

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 24533Sodium amideHCID 943013-Methyl-2-butenenitrileHCID 133196744-Diisopropylamino 2-(2-pyridyl)butyronitrile

생성물 1

HCID 542345622-(2-Diisopropylamino ethyl) 3,3-dimethyl 2-(2-pyridyl) pentane-dinitrile

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매3회

반응 조건

온도
-40 °C

실험 절차

The mixture of 4.7 g of sodium amide and 400 ml of liquid ammonia is cooled to -40° C., then the solution of 24.5 g of 4-diisopropylamino 2-(2-pyridyl) butane nitrile (Example 1a) in 30 ml of anhydrous ether is added, the temperature being maintained between -40° C. and -33° C. The mixture is stirred for 15 mins. at this temperature then the solution of 9 g of 3,3-dimethyl acrylonitrile in 40 ml of ether is added, still at the same temperature. The temperature is allowed to rise slowly up to ambient temperature (duration: about 5 hrs.). 200 ml of ether are added then water is added drop by drop. The ethereal phase is separated and the aqueous phase is re-extracted with ether. The ethereal extracts are collected and dried over sodium sulfate. The solvent is evaporated to dryness and the residue is chromatographed over a column of alumina with the eluting ethyl acetate-pentane (2.5-100) vol/vol mixture.

후처리

  1. temperaturethe temperature being maintained between -40° C. and -33° C
  2. customto rise slowly up to ambient temperature (duration: about 5 hrs.)
  3. customThe ethereal phase is separated
  4. extractionthe aqueous phase is re-extracted with ether
  5. customThe ethereal extracts are collected
  6. dry with materialdried over sodium sulfate
  7. customThe solvent is evaporated to dryness
  8. customthe residue is chromatographed over a column of alumina with the eluting ethyl acetate-pentane (2.5-100) vol/vol mixture

출처 및 근거

ORD 기록
ord-b58ef02f0aaf4f5d8b614354929b82db
출처 데이터셋
uspto-grants-1988_01
특허 번호
US04721710

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