Ethanol → 2-(2-Naphthylthiomethyl)glutaronitrile

HRID 1645781Notes

Reaction equation

HRID 1645781 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[SH:11].[CH2:12]=[C:13]([CH2:16][CH2:17][C:18]#[N:19])[C:14]#[N:15].C(O)C>CO>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11][CH2:12][CH:13]([CH2:16][CH2:17][C:18]#[N:19])[C:14]#[N:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 70582-NaphthalenethiolHCID 740802,4-Dicyano-1-butene

Product 1

HCID 198023302-(2-Naphthylthiomethyl)glutaronitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-naphthalenethiol (10.0 g), 2-methyleneglutaronitrile (6.8 ml), ethanol (150 ml), and triton B (40% methanol solution, 10 drops) was refluxed for 2 hours. After the reaction mixture was concentrated in vacuo, the resulting residue was dissolved in chloroform, washed with water, and dried over MgSO4. The solvent was evaporated at reduced pressure, and the residue was recrystallized from ethyl acetate-hexane to give 15.6 g of 2-(2-naphthylthiomethyl)glutaronitrile.

Workup

  1. temperaturewas refluxed for 2 hours
  2. concentrationAfter the reaction mixture was concentrated in vacuo
  3. dissolutionthe resulting residue was dissolved in chloroform
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated at reduced pressure
  7. customthe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-fc01067f27404697ba7e2a21419c0dc4
Source dataset
uspto-grants-1993_01
Patent number
US05177069

Reaction notes

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