2,4-Dicyano-1-butene → 2-(3,4-Dimethylphenylthiomethyl)glutaronitrile

HRID 1885608Notes

Reaction equation

HRID 1885608 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].[CH2:10]=[C:11]([CH2:14][CH2:15][C:16]#[N:17])[C:12]#[N:13]>C(O)C>[CH3:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][CH:11]([CH2:14][CH2:15][C:16]#[N:17])[C:12]#[N:13])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 740802,4-Dicyano-1-buteneHCID 877993,4-Xylenethiol

Product 1

HCID 198793432-(3,4-Dimethylphenylthiomethyl)glutaronitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 3,4-dimethylbenzenethiol (0.59 ml), 2-methyleneglutaronitrile (0.48 ml), ethanol (10 ml), and triton B (40% ethanol solution, 5 drops) was refluxed for 5 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 purified by flash column chromatography on silica by eluting with benzene/ethyl acetate (7:1) to give 1.18 g of 2-(3,4-dimethylphenylthiomethyl)glutaronitrile as an oil.

Workup

  1. temperaturewas refluxed for 5 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 purified by flash column chromatography on silica
  8. washby eluting with benzene/ethyl acetate (7:1)

Sources & evidence

ORD record
ord-132514ed429b40b0923b17ecf9c9a8ea
Source dataset
uspto-grants-1992_09
Patent number
US05145869

Reaction notes

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