Acetonitrile → 3,4-Dimethoxy-alpha[(4-methylphenyl)thio]benzeneacetonitrile

HRID 273976Notes

Reaction equation

HRID 273976 reaction equation
Cl[CH:2]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1)[C:3]#[N:4].[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>C(OCC)(=O)C.CCCCCC>[CH3:14][O:13][C:7]1[CH:6]=[C:5]([CH:2]([S:22][C:19]2[CH:20]=[CH:21][C:16]([CH3:15])=[CH:17][CH:18]=2)[C:3]#[N:4])[CH:10]=[CH:9][C:8]=1[O:11][CH3:12]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 78114-MethylbenzenethiolHCID 11430Potassium CarbonateHCID 147151992-Chloro-2-(3,4-dimethoxyphenyl)acetonitrile

Product 1

HCID 105421673,4-Dimethoxy-alpha[(4-methylphenyl)thio]benzeneacetonitrileYield 65.4%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4.12 g of α-chloro-3,4-dimethoxybenzeneacetonitrile (U.S. Pat. No. 4,833,162), 2.48 g of p-thiocresol, 2.76 g of potassium carbonate and 100 mL of acetonitrile is stirred at 65° C. overnight. After filtering off the salts, the reaction mixture is concentrated in vacuo leaving a golden oil. The oil is dissolved in a minimum amount of ethyl acetate and diluted with 3 volumes of hexane. Seeding gives 3.81 g of the desired compound as light yellow crystals.

Workup

  1. filtrationAfter filtering off the salts
  2. concentrationthe reaction mixture is concentrated in vacuo
  3. customleaving a golden oil

Sources & evidence

ORD record
ord-a6adfda3bf624cce8cb2ec246b607b90
Source dataset
uspto-grants-1995_02
Patent number
US05387685

Reaction notes

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