Dichloromethane → Benzeneacetonitrile, 3-(methylthio)-

HRID 2414248Notes

Reaction equation

HRID 2414248 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH3:10])[CH:4]=1.C1OCCOCCOCCOCCOCCOC1.[C-:29]#[N:30].[K+].ClCCl>C(#N)C>[CH3:10][S:9][C:5]1[CH:4]=[C:3]([CH2:2][C:29]#[N:30])[CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 110628871-Chloromethyl-3-methylsulfanylbenzene

Product 1

HCID 11094968Benzeneacetonitrile, 3-(methylthio)-Yield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-chloromethyl-3-methylsulfanyl-benzene (26.9 g, 0.156 mol) and 18-crown-6 (2 g, 7.8 mmol) in dry acetonitrile (100 mL) was added potassium cyanide and stirred at room temperature for 48 hours. A precipitate was formed while adding dichloromethane (400 mL). The suspension was filtered, washed with water (2×150 mL), dried (Na2SO4) concentrated and distilled under reduced pressure to give a colorless oil (22.9 g, 91%). MS: 161.9 (M+1−).

Workup

  1. customA precipitate was formed
  2. filtrationThe suspension was filtered
  3. washwashed with water (2×150 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-3631cd5e396e4de28744f610d300a8da
Source dataset
uspto-grants-2004_11
Patent number
US06812228B2

Reaction notes

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