Dimethylformamide → HCID 17989247, compound

HRID 1443273Notes

Reaction equation

HRID 1443273 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 into 158 ml of dimethylformamide with 30.1 g (211.96 mmol) of methyl iodide. 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 onto 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. additionthe reaction mixture is poured onto ice water
  2. extractionextracted three times with methyl tert-butyl ether
  3. washThe combined organic extracts are washed with water and with brine
  4. customAfter the solvent is dried
  5. customthe residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane)
  6. customare isolated

Sources & evidence

ORD record
ord-9625087593cc47ac9655c401691ed9ab
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

Loading…