Toluene → alpha-(4-Biphenylyl)-alpha-[2-(diisopropylamino)ethyl]acetonitrile

HRID 1855962

반응식

HRID 1855962 반응식
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8]#[N:9])=[CH:3][CH:2]=1.Cl[CH2:17][CH2:18][N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21].C1(C)C=CC=CC=1.[NH2-].[Na+]>O>[C:1]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:2]=[CH:3][C:4]([CH:7]([CH2:17][CH2:18][N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[C:8]#[N:9])=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 1140TolueneHCID 73122-(Diisopropylamino)ethyl chlorideHCID 24533Sodium amideHCID 358564-Biphenylacetonitrile

생성물 1

HCID 14569341alpha-(4-Biphenylyl)-alpha-[2-(diisopropylamino)ethyl]acetonitrile

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

The solution of 100 parts of α-(4-biphenylyl)acetonitrile and 90 parts of 2-chloro-N,N-diisopropylethylamine in 850 parts by volume of toluene is heated to about 80° C. and then 22 parts of sodium amide is added slowly over a period of 30 minutes keeping the temperature at 80°-85° C. The mixture is heated at 80° C. for another 30 minutes and then cooled to room temperature. 500 Parts by volume of water is then added to the mixture and the organic layer is separated and extracted with dilute hydrochloric acid. The aqueous acidic extract is made alkaline by the addition of dilute sodium hydroxide. The alkaline mixture is extracted with ether and the ether extract is dried over calcium sulfate, filtered and stripped of solvent to afford an oil which solidifies upon standing. The crude oil is crystallized from hexane to afford α-(4-biphenylyl)-α-[2-(diisopropylamino)ethyl]acetonitrile, melting at about 54°-56° C. This compound is represented by the following structural formula ##STR21##

후처리

  1. customat 80°-85° C
  2. temperaturecooled to room temperature
  3. customthe organic layer is separated
  4. extractionextracted with dilute hydrochloric acid
  5. extractionThe aqueous acidic extract
  6. additionby the addition of dilute sodium hydroxide
  7. extractionThe alkaline mixture is extracted with ether
  8. extractionthe ether extract
  9. dry with materialis dried over calcium sulfate
  10. filtrationfiltered
  11. customto afford an oil which
  12. customThe crude oil is crystallized from hexane

출처 및 근거

ORD 기록
ord-d1e959cbd9544bba970eaa8eeafaa609
출처 데이터셋
uspto-grants-1980_08
특허 번호
US04217306

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