Sodium Cyanide → 3-Methoxy-5-methylthio-4-propoxyphenyl acetonitrile

HRID 728062Notes

Reaction equation

HRID 728062 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([S:15][CH3:16])[C:10]=1[O:11][CH2:12][CH2:13][CH3:14])[CH2:6]Cl.[C-:17]#[N:18].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][C:17]#[N:18])[CH:8]=[C:9]([S:15][CH3:16])[C:10]=1[O:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 15044966HCID 15044966, compound

Product 1

HCID 150449673-Methoxy-5-methylthio-4-propoxyphenyl acetonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 16 g of 3-methoxy-5-methylthio-4-propoxybenzyl chloride in 100 ml of dry DMF was added 5 g (0.10 mole) sodium cyanide. The mixture was stirred for about 48 hours at room temperature under N2. The solution was filtered, and the filtrate was concentrated under vacuum. The residue was purified by flash column chromatography to yield 14.5 g of 3-methoxy-5-methylthio-4-propoxyphenyl acetonitrile as an oil. (95% yield).

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated under vacuum
  3. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-96dc13ddc31b44d1927471b29f0b28b2
Source dataset
uspto-grants-1991_09
Patent number
US05047420

Reaction notes

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