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

HRID 1855962

Reaction equation

HRID 1855962 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

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##

Workup

  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

Sources & evidence

ORD record
ord-d1e959cbd9544bba970eaa8eeafaa609
Source dataset
uspto-grants-1980_08
Patent number
US04217306

Linked notes

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