Thiophenol → 2-[(Phenylsulfanyl)methyl]pentanedinitrile

Reaction equation

[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH2:10]=[C:11]([CH2:14][CH2:15][C:16]#[N:17])[C:12]#[N:13]>>[C:1]1([S:7][CH2:10][CH:11]([CH2:14][CH2:15][C:16]#[N:17])[C:12]#[N:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 3

HCID 7969Thiophenol

HCID 14798Sodium Hydroxide

HCID 740802,4-Dicyano-1-butene

Product 1

HCID 100591792-[(Phenylsulfanyl)methyl]pentanedinitrile

Procedure

A mixture of thiophenol (3.63 g.), 2N aqueous sodium hydroxide (25 ml.) and 2-methyleneglutaronitrile (3.2 g.) was stirred at room temperature for 18 hours. The mixture was extracted with diethyl ether, and the ether extract washed with water and then dried and evaporated to dryness to give 2-(phenylthiomethyl)glutaronitrile which was used without further purification.