Potassium Cyanide → HCID 19362515, compound

HRID 850263Notes

Reaction equation

HRID 850263 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]Cl)=[CH:5][C:4]=1[S:11][CH3:12].[C-:13]#[N:14].[K+]>CS(C)=O>[CH3:12][S:11][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:3]=1[S:2][CH3:1])[CH2:9][C:13]#[N:14]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 19362524HCID 19362524, compound

Product 1

HCID 19362515HCID 19362515, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

42.5 g (0.194 mol) of 1,2-bis(methylthio)-4-chloromethyl-benzene and 25.3 g (0.388 mol) of potassium cyanide are stirred at ambient temperature in 200 ml of DMSO. When the starting material can no longer be detected by GC analysis, the brown solution is poured into ice/water and extracted with acetic acid acetate and the organic phase is dried over magnesium sulfate. After evaporation 34.8 g (85.7%) of 3,4-bis(methylthio)-benzyl cyanide are obtained as brown substance. The 1H-NMR-spektra data (CDCl3) are in accordance with the proposed structure of the compound: 7.24-7.06 ppm (s and d, 3 aromatic H), 3.70 ppm (s, 2H), 2.47 ppm (s, CH3S) and 2.45 ppm (2 s, CH3S).

Workup

  1. extractionextracted with acetic acid acetate
  2. dry with materialthe organic phase is dried over magnesium sulfate
  3. customAfter evaporation 34.8 g (85.7%) of 3,4-bis(methylthio)-benzyl cyanide
  4. customare obtained as brown substance
  5. custom7.24-7.06 ppm (s and d, 3 aromatic H), 3.70 ppm (s, 2H), 2.47 ppm (s, CH3S) and 2.45 ppm (2 s, CH3S)

Sources & evidence

ORD record
ord-f4624bfed07a49d28a0d41a11fc928fb
Source dataset
uspto-grants-2000_01
Patent number
US06017675

Reaction notes

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