Ethanol → 2-(3,4-Dichlorophenylthiomethyl)glutaronitrile

HRID 1885601Notes

Reaction equation

HRID 1885601 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:10]=[C:11]([CH2:14][CH2:15][C:16]#[N:17])[C:12]#[N:13].C(O)C>CO>[Cl: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[Cl:8]

Participants

5

Reactant 3

HCID 702EthanolHCID 740802,4-Dicyano-1-buteneHCID 799643,4-Dichlorobenzenethiol

Product 1

HCID 198793522-(3,4-Dichlorophenylthiomethyl)glutaronitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3,4-dichlorobenzenethiol (3.00 ml), methyleneglutaronitrile (2.57 ml), ethanol (25 ml), and triton B (40% methanol solution, 10 drops) was refluxed for 4 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 diethyl ether-hexane to give 6.14 g of 2-(3,4-dichlorophenylthiomethyl)glutaronitrile.

Workup

  1. temperaturewas refluxed for 4 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 diethyl ether-hexane

Sources & evidence

ORD record
ord-6cc0bbfeb3ad4443b7da709c89e08b7d
Source dataset
uspto-grants-1992_09
Patent number
US05145869

Reaction notes

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