Dimethylformamide → HCID 68829363, compound

HRID 747714Notes

Reaction equation

HRID 747714 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=3)[C:23]#[N:24])[O:13]CC(C)(C)CO2)=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].[CH3:33][N:34](C)C=O>[Cu+]>[C:23]([C:22]1[CH:21]=[C:20]([CH:27]=[CH:26][CH:25]=1)[O:19][CH2:18][CH2:17][CH2:16][C:8]([C:5]1[CH:4]=[CH:3][C:2]([C:33]#[N:34])=[CH:7][CH:6]=1)=[O:13])#[N:24]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 688339843-[3-[2-(4-Bromophenyl)-5,5-dimethyl-1,3-dioxane-2-yl]propoxy]benzonitrile

Product 1

HCID 68829363HCID 68829363, compound

Reagents, catalysts & solvents 1

HCID 104815Copper(1+)Catalyst

Procedure

500 mg (1.16 mmol) of 3-[3-[2-(4-bromophenyl)-5,5-dimethyl-1,3-dioxane-2-yl]propoxy]benzonitrile and 114 mg (1.27 mmol) of copper (1) cyamide were stirred in 1 ml of dimethylformamide at 140° C. overnight. Saturated aqueous sodium hydrogencarbonate solution was added to the resultant mixture. After the extraction with ethyl acetate, the organic layer was washed with saturated aqueous NaCl solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated. 10 ml of ethanol and 2 ml of 6 N hydrochloric acid were added to the residue, and the resultant mixture was heated under reflux for 5 hours. The solvent was evaporated. 1 N hydrochloric acid was added to the residue. After the extraction with ethyl acetate, the extract was washed with saturated aqueous NaCl solution and then dried over anhydrous magnesium sulfate. The solvent was evaporated. The residue was purified by the silica gel chromatography with ethyl acetate hexane as the extractant to obtain the title compound.

Workup

  1. extractionAfter the extraction with ethyl acetate
  2. washthe organic layer was washed with saturated aqueous NaCl solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. addition10 ml of ethanol and 2 ml of 6 N hydrochloric acid were added to the residue
  6. temperaturethe resultant mixture was heated
  7. temperatureunder reflux for 5 hours
  8. customThe solvent was evaporated
  9. addition1 N hydrochloric acid was added to the residue
  10. extractionAfter the extraction with ethyl acetate
  11. washthe extract was washed with saturated aqueous NaCl solution
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customThe solvent was evaporated
  14. customThe residue was purified by the silica gel chromatography with ethyl acetate hexane as the extractant

Sources & evidence

ORD record
ord-243edebb27d047ca8cb43dc41093ea53
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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