Thiophenol → 2-[(Phenylsulfanyl)methyl]pentanedinitrile

HRID 652293Notes

Reaction equation

HRID 652293 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

4

Reactant 3

HCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 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.

Workup

  1. extractionThe mixture was extracted with diethyl ether
  2. extractionthe ether extract
  3. washwashed with water
  4. customdried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-adf5cc9a29534517bcb85d14c634c86b
Source dataset
uspto-grants-1987_06
Patent number
US04670592

Reaction notes

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