Dimethylformamide → HCID 69186027, compound

HRID 2078418Notes

Reaction equation

HRID 2078418 reaction equation
Cl.F[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][CH2:14]N1CC2OC(CNC2)C1)[C:6]#[N:7].[Br:24]CCCBr.C([O-])([O-])=O.[K+].[K+].C[N:36]([CH:38]=O)C>>[Br:24][CH2:14][CH2:13][CH2:12][O:11][C:10]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:38]#[N:36]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 86628045HCID 86628045, compound

Product 1

HCID 69186027HCID 69186027, compoundYield 63%

Conditions

Temperature
60 °C

Procedure

4-Hydroxyisophthalonitrile (4.4 g, 0.03 mol; see step (iii) above) was dissolved in dry DMF (100 mL). 1,3-Dibromopropane (36 g, 0.12 mol) and K2CO3 (8.2 g, 0.06 mol) were added. Then the reaction mixture was then stirred at 60° C. for 15 h before being cooled to RT and filtered through a Celite® bed. The filtrate was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel, using 2% ethyl acetate in petroleum ether as eluent, to yield the title compound (5.1 g, 63%) as pale yellow solid.

Workup

  1. temperaturebefore being cooled to RT
  2. filtrationfiltered through a Celite® bed
  3. additionThe filtrate was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-efcf82098ff841cf8097ef5933b3672c
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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