Dimethylformamide → HCID 12343242, compound

HRID 1730169Notes

Reaction equation

HRID 1730169 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.CN(C)C=O.[H-].[Na+].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:9]#[N:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 80571-BromopentaneHCID 24758Sodium hydrideHCID 68016Benzeneacetonitrile, 4-fluoro-

Product 1

HCID 12343242HCID 12343242, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and cooled (ice-bath) solution of 27 parts of 4-fluorobenzeneacetonitrile in 180 parts of N,N-dimethylformamide are added 6.2 parts of sodium hydride dispersion 78% and the whole is stirred for 1 hour while cooling. Then there are added dropwise 31 parts of 1-bromopentane. Upon completion, stirring is continued for 2 hours at room temperature. The reaction mixture is poured onto 1000 parts of water and the product is extracted twice with 2,2'-oxybispropane. The combined extracts are washed three times with water, dried, filtered and evaporated. The residue is distilled, yielding 21 parts of 4-fluoro-α-pentylbenzeneacetonitrile; bp. 85°-93° C at 0.1 mm. pressure.

Workup

  1. stirringthe whole is stirred for 1 hour
  2. temperaturewhile cooling
  3. stirringUpon completion, stirring
  4. extractionthe product is extracted twice with 2,2'-oxybispropane
  5. washThe combined extracts are washed three times with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. distillationThe residue is distilled

Sources & evidence

ORD record
ord-01769cadab494428b7fd614dd27c6aa1
Source dataset
uspto-grants-1976_11
Patent number
US03991201

Reaction notes

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