Methyl iodide → HCID 21406512, compound

HRID 1729896Notes

Reaction equation

HRID 1729896 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:14][C:15]#[N:16].[H-].[Na+].[H][H].[CH3:21]I>CN(C)C=O>[CH3:21][CH:14]([C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:12][C:13]=2[CH:1]=1)[C:15]#[N:16]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12433608HCID 12433608, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21406512HCID 21406512, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of fluorene-2-acetonitrile (2g.) in dimethylformamide is treated with sodium hydride (415mg.) portionwise while stirring under nitrogen. After the evolution of hydrogen has ceased, the mixture is cooled to 10°-15° and treated dropwise with methyl iodide (2.82g.) in dimethylformamide (10ml.). After stirring for 30 minutes, the ice bath is removed and the mixture stirred at room temperature overnight. The reaction mixture is then poured into ice water and extracted with ether. The ether extracts are washed with water, dried (MgSO4) and evaporated to give the title compound.

Workup

  1. temperaturethe mixture is cooled to 10°-15°
  2. stirringAfter stirring for 30 minutes
  3. customthe ice bath is removed
  4. stirringthe mixture stirred at room temperature overnight
  5. additionThe reaction mixture is then poured into ice water
  6. extractionextracted with ether
  7. washThe ether extracts are washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-9efff9b34695432aba39fde46fbdfc9e
Source dataset
uspto-grants-1976_11
Patent number
US03989841

Reaction notes

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