Chloroacetonitrile → (3,4-Dimethoxy-phenylsulfanyl)-acetonitrile

HRID 458796

Reaction equation

HRID 458796 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl[CH2:13][C:14]#[N:15].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][CH2:13][C:14]#[N:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 7856ChloroacetonitrileHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1365393,4-Dimethoxybenzene-1-thiol

Product 1

HCID 12698215(3,4-Dimethoxy-phenylsulfanyl)-acetonitrileYield 84%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3,4-dimethoxythiophenol (5.0 g, 29.4 mmol) in dry DMF (150 ml), were added chloroacetonitrile (1.85 ml, 29.4 mmol), anhydrous K2CO3 (6.09 g, 44.1 mmol) and DMAP (358 mg, 2.9 mmol). The reaction mixture was stirred at 80° C. for 20 h under nitrogen. After cooling, the mixture was filtered and concentrated in vacuo. The residue was combined with H2O, extracted with CH2Cl2, the combined organic phases were dried over anhydrous MgSO4, filtered and concentrated to give a crude oil. Flash chromatography (AcOEt) gave the title product (5.16 g, 84%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated in vacuo
  4. extractionextracted with CH2Cl2
  5. dry with materialthe combined organic phases were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude oil

Sources & evidence

ORD record
ord-0035c8957c2f4741b38e3f5d494f953c
Source dataset
uspto-grants-2007_03
Patent number
US07192950B2

Linked notes

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