Hydrochloric Acid → HCID 68736409, compound

HRID 1474068Notes

Reaction equation

HRID 1474068 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]#[N:13].[C:14](=O)([O:22]C1C=CC=CC=1)[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>O1CCCC1>[C:12]([CH:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[O:4][CH3:3])[C:14]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:22])#[N:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7597Diphenyl carbonateHCID 24758Sodium hydrideHCID 81496(2-Methoxyphenyl)acetonitrile

Product 1

HCID 68736409HCID 68736409, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of sodium hydride (3.39 g of 60% in mineral oil, 84.9 mmol) in tetrahydrofuran (200 mL) at room temperature was added 2-(2-methoxyphenyl)acetonitrile (10.0 g, 67.9 mmol) dropwise. The reaction mixture was then heated to reflux and the gray suspension turned dark red over 30 min. Diphenyl carbonate (18.2 g, 84.9 mmol) was added portionwise, and the reaction suspension was heated at reflux for an additional 18 h. The reaction mixture was cooled, poured into 1 N HCl (200 mL) and extracted with ethyl acetate (3×200 mL). The organic phases were combined, dried over magnesium sulfate, filtered and concentrated onto Celite® under reduced pressure. The resultant residue was purified by chromatography on silica gel using 10-90% ethyl acetate/hexane as eluant to give the title compound as a light yellow solid (14.3 g).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux
  3. temperaturethe reaction suspension was heated
  4. temperatureat reflux for an additional 18 h
  5. temperatureThe reaction mixture was cooled
  6. extractionextracted with ethyl acetate (3×200 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated onto Celite® under reduced pressure
  10. customThe resultant residue was purified by chromatography on silica gel using 10-90% ethyl acetate/hexane as eluant

Sources & evidence

ORD record
ord-085f2f0ec895412eb09bf700d17a61e3
Source dataset
uspto-grants-2015_04
Patent number
US09018220B2

Reaction notes

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