Dimethylformamide → HCID 17989247, compound

HRID 1869454Notes

Reaction equation

HRID 1869454 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#N)=[CH:4][C:3]=1[O:11][CH3:12].[CH3:13]I.[H-].[Na+].C[N:18]([CH3:21])C=O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:9])[C:21]#[N:18])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 17989296(4-Fluoro-3-methoxyphenyl)acetonitrile

Product 1

HCID 17989247HCID 17989247, compound

Procedure

16.67 g (100.93 mmol) of (4-fluoro-3-methoxyphenyl)-acetonitrile is introduced with 30.1 g (211.96 mmol) of methyliodide into 158 ml of dimethylformamide. At 0° C., 8.50 g (211.96 mmol) of a 55-60% sodium hydride suspension is added in portions. After stirring overnight at room temperature, the reaction mixture is poured into ice water and then extracted three times with methyl tert-butyl ether. The combined organic extracts are washed with water and with brine. After the solvent is dried and spun off, the residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane). 5.11 g (26.2%) of the desired compound and 6.18 g of the monomethyl compound, which is realkylated, are isolated.

Workup

  1. extractionextracted three times with methyl tert-butyl ether
  2. washThe combined organic extracts are washed with water and with brine
  3. customAfter the solvent is dried
  4. customthe residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane)
  5. customare isolated

Sources & evidence

ORD record
ord-d93f453fa26c43dab11f8db8c11c7c8b
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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