Dimethyl Sulfoxide → 2-(4-Chlorophenyl)-5-phenylvaleronitrile

HRID 5938

Reaction equation

HRID 5938 reaction equation
[OH-].[Na+].CS(C)=O.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]#[N:16])=[CH:10][CH:9]=1.Br[CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH2:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]#[N:16])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 12503(3-Bromopropyl)benzeneHCID 14798Sodium HydroxideHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 141477222-(4-Chlorophenyl)-5-phenylvaleronitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 ml of an aqueous sodium hydroxide (1.08 g) solution was added to a 10 ml solution of dimethylsulfoxide containing 1.0 g (6.6 mmole) of 4-chlorophenylacetonitrile and 1.3 g (6.6 mmole) of 1-bromo-3-phenylpropane at room temperature. After stirring for 2 hours under the same conditions, water was added to the reaction mixture and the mixture was extracted with 10 ml of n-hexane, dried, and condensed under reduced pressure to obtain 1.78 g (yield: quantitative) of 2-(4-chlorophenyl)-5-phenylvaleronitrile.

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe mixture was extracted with 10 ml of n-hexane
  3. customdried
  4. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-fc328861075c4601a239c2cf487b943a
Source dataset
uspto-grants-1993_09
Patent number
US05246958

Linked notes

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